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On Second Thought

A surge of weekend homeowners pushes boundaries



Rouge owner Maggie Merelle mingles with patrons. The bar has a fairly even mix of locals, visitors, and part-time residents who have found their “spot.”

Photo by Scott Barrow

Berkshire County has long been an escape for city dwellers looking to breathe fresh country air. The Rockefellers, the Morgans, the Melvilles—all set up grand cottages in the region, many of which have become historical destinations. But the swell of second homeowners, especially in the last decade, has caused a cultural shift even in the remotest Berkshire towns, forcing full-timers to rethink their idea of “community.”

“The economy for contractors is good in this town, and that’s because we have second homeowners,” says Sheffieldbased builder Ralph Lombardi. He moved to the Berkshires— “from the rat race” in New Jersey—nearly 25 years ago to raise a family and build a business as a contractor. At least half his clientele are part-time residents who call him every time they need work done. The repeat business is his lifeblood, especially through the slow winter months.

“Around January and February things get pretty slow,” Lombardi says. “But I can rely on steady work, especially leading up to the holidays— Memorial Day, Thanksgiving, Christmas, early spring—because second homeowners are coming here year-round, almost every weekend.”

The number of part-time residents in the Berkshires has climbed to nearly 30 percent, according to a recent report issued by the Berkshire Taconic Community Foundation. The percentage of housing units used as second homes ranges from a whopping 60 percent in Otis (57 percent in neighboring Monterey) to a still-sizable 34 percent or so in places like Alford, Egremont, New Marlborough, and Mount Washington. Conversely, many of the towns with the highest second-ownership rates also have the most cost-burdened renters, meaning that more than 30 percent (often closer to 40 percent) of their monthly earnings goes toward rent. This is a “growing pain” of a community ripe with opportunity, says Maggie Merelle, co-owner of Rouge restaurant in West Stockbridge, and a real-estate agent for William Pitt Sotheby’s.

“When we first opened Rouge 16 years ago, I was told by another local business owner that we’d never make it. I mean, West Stockbridge then, there was tumbleweed in the street,” says Merelle. “But we survived by becoming a destination. We’re constantly reinventing ourselves throughout the year with wine dinners, burger night, and social media. It’s a hustle.”

On any given evening, the bar at Rouge is a fairly even mix of Berkshire locals, visitors from nearby Albany, and part-time residents who have found their “spot.” This growing mélange is what inspired Merelle to try her hand at real estate. She says most of her clients hail from Boston, New York, the West Coast, and, more recently, Washington, D.C. And she sees their interest in the area as beneficial to full-time residents.

“This is not your typical vacation town,” Merelle says. “We have people who come here loyally on the weekends and want to be a part of this community. And many local people have made a decent living, and retirement for that matter, off of the consistent business of second homeowners.”

Chuck Leach, president of Lee Bank, is also heartened by the influx of second homeowners. As a member of a focus group for the Berkshire Taconic report (which includes data from neighboring Dutchess, Columbia, and Litchfield counties), he says issues such as the opioid epidemic, growing poverty rates, a lack of skilled workers, and a lack of affordable housing are not surprising revelations.

“There is a sort of issue fatigue that people are feeling,” Leach says. “And yes, the issues that are highlighted in the report—especially jobs and the economy, and infrastructure—need to be addressed. But the people coming here really want to put down roots and invest in the community. They really like the local aspect. They like getting involved, and they have the savvy and the capital to do that. That’s a definite positive.”

It’s not just parttime residents who are looking to invest in the Berkshires. Leach says that at least 50 percent of Lee Bank clients are longtime residents and business owners who have worked hard for years and are looking for help managing the fruits of their labors, which is why the bank has added investment and planning services to its roster of products. Because of the changing demographic, the bank, much like many other businesses across the county, decided to expand its scope beyond the “typical community-bank model.”

“Independent community banks have a tremendous amount of opportunity ahead,” Leach says. “However, we need to be on our game. We need to evolve and remain proactive. The alternative is that we run the risk of becoming irrelevant.”

Cultural institutions are taking that advice to heart. In fact, many are leading the way as architects of a “creative hospitality” model that is driving the area’s economy as waves of visitors to the Berkshires transition to becoming part-time residents. Rebecka McDougall, communications director at The Mount in Lenox, says a key element to survival is to step out of the seasonal bubble.

“Typically, the Mount will close for the season at the end of October, and then we will go into the off-season programming,” she says. “But in talking with other businesses—B&B owners, retailers—it became important to be open for more than that. People need access to culture during all the months. They look forward to it, it’s a big draw, and it’s important to staying relevant to the local population as well as encouraging second homeowners to come back every weekend. It’s a symbiotic relationship. Why is that a bad thing?”

It’s not for Lombardi, who has benefited from having solid relationships with all his clients, especially part-time residents. “I own my own home. I have a good life, in a beautiful place. Why bite the hand that feeds me?”

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Greenwich, CT  06830
View map »


Sponsor: Bruce Museum
Website »

More information

Heather Gaudio Fine Art is pleased to announce “Paradigm Shifts,” a group exhibition featuring paintings by Charles Arnoldi, Ricardo Mazal and Manuel Mérida.  The show opens...

Cost: Free

Where:
Heather Gaudio Fine Art
66 Elm Street
New Canaan, CT  06840
View map »


Sponsor: Heather Gaudio Fine Art
Telephone: (203)801-9590
Contact Name: Rachael Palacios
Website »

More information

Sports and recreation are universal experiences. Whether we make it to the big leagues or never leave our backyards, these activities play important roles in our lives. They help us form...

Cost: Free!

Where:
Litchfield History Museum
7 South Street
Litchfield, CT  06759
View map »


Sponsor: Litchfield Historical Society
Telephone: 860-567-4501
Contact Name: Megan Olver
Website »

More information

The Litchfield Historical Society is pleased to announce the opening of a new exhibit Thoughts, Words, and Deeds: Exploring the Litchfield Female Academy, on view April 22 through November 27, 2017...

Cost: Free

Where:
Litchfield History Museum
7 South Street
Litchfield, CT  06759
View map »


Sponsor: Litchfield Historical Society
Telephone: 860-567-4501
Contact Name: Megan Olver
Website »

More information

Tuesdays. Ages 13 and up. Multi-instrumentalist, teacher and performer Rob Sanzone will teach ukulele technique, chord progressions and songs from many musical genres. A limited number of...

Cost: Free

Where:
Berkshire South Regional Community Center
15 Crissey Road
Great Barrington , MA  01230
View map »


Sponsor: Berkshire South Regional Community Center
Telephone: 4135282810, ext. 31
Contact Name: Kristen
Website »

More information

Ages 13 and up. Multi-instrumentalist, teacher and performer Rob Sanzone will teach ukulele technique, chord progressions and songs from many musical genres. A limited number of ukuleles are...

Cost: Free, Open to members and guests.

Where:
Berkshire South Regional Community Center
15 Crissey Road
Great Barrington, MA  01230
View map »


Website »

More information

 The Mattatuck Museum presents “The Valley Girls” with an exhibit running from September 10 – November 12, 2017.  A special reception will be held on Sunday, September...

Cost: Fee for Admission

Where:
Mattatuck Museum
144 West Main St
Waterbury, CT
View map »


Sponsor: Mattatuck Museum
Telephone: 203-753-0381
Contact Name: Mally DeSomma
Website »

More information

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For over 30 years, Green Chimneys has been opening its doors to the community for Little Folk Farm Day, welcoming scores of young people to explore our bustling Brewster campus. Play groups,...

Cost: infants under 2 - Free; Adults - Free; Children 2 & older -@ $10

Where:
Green Chimneys
400 Doansburg Rd.
Brewster, NY  10509
View map »


Sponsor: Green Chimneys
Telephone: 845-279-2995 ext 307
Contact Name: Gail Dickerman
Website »

More information

Apple Picking Has Begun! Picking Hours: Our orchard is open daily from 9am - 4:30pm. Festival Weekends 10am - 5pm: 9/9-10 9/16-17 9/21-24 9/30-10/1 Pizza Party at...

Where:
Harvest Moon Farm & Orchard
130 Hardscrabble Road
North Salem, NY
View map »


Website »

More information

Cruise through history and the majestic beauty of the Hudson River We specialize in Weddings and Private Charters Elegance for all affairs 2 Hour narrated sightseeing cruises Customized cruises...

Cost: Adults $22 Seniors Ages 65 and up $20 Children Ages 4 to 11 $18

Where:
Hudson River Adventures, Inc
90 Front St
Newburgh, NY
View map »


Website »

More information

The Pound Ridge Historical Society will open “Modern in Pound Ridge: 20th Century Architecture + Lifestyle” at the Pound Ridge Museum on April 23, 2017. This is a real departure for the...

Cost: Free

Where:
Pound Ridge Museum
255 Westchester Ave
Pound Ridge, NY  10576
View map »


Sponsor: Pound Ridge Historical Society
Telephone: 914-764-4333
Website »

More information

Improvisation, where music is concerned, is the act of composing or arranging without previous preparation. It is also a hallmark of traditional jazz and what Spyro Gyra lives and breathes. Taking...

Cost: $75 Standard

Where:
FTC StageOne
70 Sanford St
Fairfield, CT  06824
View map »


Telephone: 120-325-91036
Contact Name: Box Office
Website »

More information

Every summer, the Seaport Ferry in South Norwalk carries hundreds of hungry passengers to the historic 1868 Sheffield Island Lighthouse for the Norwalk Seaport Association's famous Thursday...

Cost: $65 or $79 per person

Where:
Sheffield Island & Lighthouse
4 North Water Street
Norwalk, CT
View map »


Website »

More information

193 Danbury Road, Ridgefield; 203-431-7000. founders-hall.org SEPT 27 @ 6 PM.  Wine, Cheese & Accessories, a Ladies Night Out; a fun evening of fine wine, food, fellowship,...

Cost: $20

Where:
Founders Hall
193 Danbury Road
Ridgefield, CT  06877
View map »


Sponsor: Founders Hall
Telephone: 203-431-7000
Contact Name: Laurie Christiansen
Website »

More information

Join Dr. Mara Davidson and Dr. Andrew Cummins of the Shalva Clinic in Westport to discover some of the causes of anxiety and digestive problems and natural ways to treat these conditions. Some of...

Cost: Free

Where:
Pequot Library
720 Pequot Avenue
Southport, CT  06890
View map »


Sponsor: Pequot Library
Telephone: 203-259-0346 ext.115
Contact Name: Front Desk
Website »

More information

Hilltop Hanover Farm proudly offers freshly harvested seasonal produce, herbs, and cut flowers at our farm stand. You can find your usual favorites as well as unique heirloom...

Where:
Hilltop Hanover Farm & Environmental Center
Hilltop Hanover Farm
Yorktown Heights, NY  10598
View map »


Website »

More information

Experience the joy of setting sail and shutting off the engine as we sail through Long Island Sound. Sit back and relax or take a turn at the helm, the choice is yours. Sails depart from...

Cost: $20-$40

Where:
SoundWaters
1281 Cove Rd
Stamford, CT
View map »


Website »

More information

The King of Navarre and his lords have sworn off the pleasures of life to pursue their studies, but can their oaths hold up when a princess and her ladies come to town? Men and women test their own...

Cost: $15.75-$57.75

Where:
Hudson Valley Shakespeare Festival
1601 Rt. 9D
Garrison, NY
View map »


Website »

More information

The Faire is a rollicking romp through Elizabethan England complete with 16th Century games, rides, arts, crafts, food, music and dance – set within the majestic groves of Tuxedo Park, New...

Cost: $25 for adults, $20 for military and age 62+, $12 for age 5-12, free for age 4-

Where:
600 Rt. 17A
Tuxedo Park, NY
View map »


Website »

More information

This festival aims to serve as a creative outlet to residents of greater New Milford by providing them with the opportunity to show their work on the big screen, all while raising money for a...

Cost: varies but mostly free

Where:
Bank Street Theater
46 Bank St
New Milford, CT
View map »


Website »

More information

Our founder, Cole Palen, grew up next to a great 1930’s Hudson Valley airport dreaming that he would own and fly the machines he saw overhead and spent the rest of his life bringing the...

Cost: $8.00 - $10.00

Where:
Old Rhinebeck Aerodrome
9 Norton Rd
Red Hook, NY
View map »


Website »

More information

Nikon Small World  exhibition runs July 29 - October 29, 2017 at Bruce Museum This exhibit showcases the top 20 award-winning photographs of the 42nd annual Nikon Small World...

Cost: $10 adult,$8 senior/student, under 5 and member free. Free on Tuesdays to all

Where:
Bruce Museum
1 Museum Drive
Greenwich, CT  06830
View map »


Sponsor: Bruce Museum
Website »

More information

Heather Gaudio Fine Art is pleased to announce “Paradigm Shifts,” a group exhibition featuring paintings by Charles Arnoldi, Ricardo Mazal and Manuel Mérida.  The show opens...

Cost: Free

Where:
Heather Gaudio Fine Art
66 Elm Street
New Canaan, CT  06840
View map »


Sponsor: Heather Gaudio Fine Art
Telephone: (203)801-9590
Contact Name: Rachael Palacios
Website »

More information

Sports and recreation are universal experiences. Whether we make it to the big leagues or never leave our backyards, these activities play important roles in our lives. They help us form...

Cost: Free!

Where:
Litchfield History Museum
7 South Street
Litchfield, CT  06759
View map »


Sponsor: Litchfield Historical Society
Telephone: 860-567-4501
Contact Name: Megan Olver
Website »

More information

The Litchfield Historical Society is pleased to announce the opening of a new exhibit Thoughts, Words, and Deeds: Exploring the Litchfield Female Academy, on view April 22 through November 27, 2017...

Cost: Free

Where:
Litchfield History Museum
7 South Street
Litchfield, CT  06759
View map »


Sponsor: Litchfield Historical Society
Telephone: 860-567-4501
Contact Name: Megan Olver
Website »

More information

The Smithy Loft Gallery is pleased to announce a new exhibit featuring infrared photography by Litchfield, CT photographer, Wendy Costa, and contemporary drawings and paintings by Stony Creek, CT...

Cost: Free

Where:
Loft Gallery @ The Smithy Store
10 Main Street
New Preston, CT  06777
View map »


Sponsor: The Smithy Store
Telephone: 860-868-9003
Contact Name: Susan Newbury
Website »

More information

Wednesdays, 6:45-8:15 p.m.  Ages 13 and up. Sing to your heart’s content under the guidance and accompaniment of musician and teacher Robert Kelly. Songs will include pop, folk, jazz...

Cost: FREE! Open to members and guests.

Where:
Berkshire South Regional Community Center
15 Crissey Road
Great Barrington, MA  01230
View map »


Website »

More information

Does speaking before a group make you totally anxiety ridden?  Whether for business or volunteer work, Whether you have to speak in front of large groups for work or you have a big event...

Cost: $240

Where:
Ridgefield Playhouse
80 East Ridge
Ridgefield, CT  06877
View map »


Telephone: 203-438-5795
Website »

More information

 The Mattatuck Museum presents “The Valley Girls” with an exhibit running from September 10 – November 12, 2017.  A special reception will be held on Sunday, September...

Cost: Fee for Admission

Where:
Mattatuck Museum
144 West Main St
Waterbury, CT
View map »


Sponsor: Mattatuck Museum
Telephone: 203-753-0381
Contact Name: Mally DeSomma
Website »

More information

Show More...
Show Less...

Apple Picking Has Begun! Picking Hours: Our orchard is open daily from 9am - 4:30pm. Festival Weekends 10am - 5pm: 9/9-10 9/16-17 9/21-24 9/30-10/1 Pizza Party at...

Where:
Harvest Moon Farm & Orchard
130 Hardscrabble Road
North Salem, NY
View map »


Website »

More information

Thursday, Sept. 28. The New York Unit of the Herb Society of America presents the 69th Annual Herb Fair, from 11 a.m. to 2 p.m. at John Jay Homestead, 400 Route 22, Katonah. Admission is free;...

Cost: Free admission; fee for lunch

Where:
John Jay Homestead State Historic Site
400 Route 22
Katonah, NY  10536
View map »


Sponsor: N.Y. Unit of Herb Society of America
Telephone: (914) 232-5651
Contact Name: Toby Baker
Website »

More information

Cruise through history and the majestic beauty of the Hudson River We specialize in Weddings and Private Charters Elegance for all affairs 2 Hour narrated sightseeing cruises Customized cruises...

Cost: Adults $22 Seniors Ages 65 and up $20 Children Ages 4 to 11 $18

Where:
Hudson River Adventures, Inc
90 Front St
Newburgh, NY
View map »


Website »

More information

The Pound Ridge Historical Society will open “Modern in Pound Ridge: 20th Century Architecture + Lifestyle” at the Pound Ridge Museum on April 23, 2017. This is a real departure for the...

Cost: Free

Where:
Pound Ridge Museum
255 Westchester Ave
Pound Ridge, NY  10576
View map »


Sponsor: Pound Ridge Historical Society
Telephone: 914-764-4333
Website »

More information

Celebrated royal writer Sally Bedell Smith discusses her New York Times best-selling biography, Prince Charles: The Passions and Paradoxes of an Improbable Life.

Cost: $30 general; $25 Mount members

Where:
The Stable at The Mount
2 Plunkett St
Lenox, MA  01240
View map »


Sponsor: www.edithwharton.org/event/sally-bedell-smiths-prince-charles/?instance_id=18695

More information

The 2017 DownStreet Art season will celebrate its finale on Thursday, September 28th. The evening will feature a performance by Magic Lantern Theater. Performing on the BOOM Music Stage under the...

Cost: Free

Where:
DownStreet Art
51 Main Street
North Adams, MA  01247
View map »


Sponsor: DownStreet Art
Telephone: 413-662-5253
Contact Name: Michelle Daly
Website »

More information

WHAT: Hospice of Westchester (HOW) will host its annual “In Celebration” Gala Cocktail Reception on Thursday, September 28. The special guest speaker for the evening will be Emmy...

Cost: $300

Where:
Westchester Country Club
99 Biltmore Avenue
Rye, NY, NY  10580
View map »


Telephone: 914-682-1484
Contact Name: Holly Benedict
Website »

More information

Every summer, the Seaport Ferry in South Norwalk carries hundreds of hungry passengers to the historic 1868 Sheffield Island Lighthouse for the Norwalk Seaport Association's famous Thursday...

Cost: $65 or $79 per person

Where:
Sheffield Island & Lighthouse
4 North Water Street
Norwalk, CT
View map »


Website »

More information

The White Hart Speaker Series is presented in collaboration with Oblong Books & Music & Scoville Memorial Library ADMISSION IS FREE.  THE PURCHASE OF A BOOK AT THE EVENT SUPPORTS...

Cost: Free

Where:
White Hart Inn
15 Under Mountain Road
Salisbury, CT
View map »


Website »

More information

Ages 18 and Older Chef Deborah Miller Menu:   Curried Corn Chowder – Black Bean and Andouille Sausage Soup  – Baked Potato and Leek Soup with Cheddar and Bacon...

Cost: $75 per person - Full Participation

Where:
The Silo
44 Upland Road
New Milford, CT  06776
View map »


Sponsor: The Silo
Telephone: 860-355-0300
Contact Name: kim Prange
Website »

More information

Consider you and your plus one cordially invited to the Bridal Event of the season! Wedding OR Knot makes its debut at the beautiful Sheraton Stamford located at 700 E. Main Street, Stamford, CT on...

Cost: $10

Where:
Sheraton Stamford Hotel
700 East Main Street
Stamford, CT  06904
View map »


Sponsor: Clear Vision Productions
Telephone: 203-745-4946
Contact Name: Charlene Chiaro
Website »

More information

Hilltop Hanover Farm proudly offers freshly harvested seasonal produce, herbs, and cut flowers at our farm stand. You can find your usual favorites as well as unique heirloom...

Where:
Hilltop Hanover Farm & Environmental Center
Hilltop Hanover Farm
Yorktown Heights, NY  10598
View map »


Website »

More information

Experience the joy of setting sail and shutting off the engine as we sail through Long Island Sound. Sit back and relax or take a turn at the helm, the choice is yours. Sails depart from...

Cost: $20-$40

Where:
SoundWaters
1281 Cove Rd
Stamford, CT
View map »


Website »

More information

The King of Navarre and his lords have sworn off the pleasures of life to pursue their studies, but can their oaths hold up when a princess and her ladies come to town? Men and women test their own...

Cost: $15.75-$57.75

Where:
Hudson Valley Shakespeare Festival
1601 Rt. 9D
Garrison, NY
View map »


Website »

More information

The Faire is a rollicking romp through Elizabethan England complete with 16th Century games, rides, arts, crafts, food, music and dance – set within the majestic groves of Tuxedo Park, New...

Cost: $25 for adults, $20 for military and age 62+, $12 for age 5-12, free for age 4-

Where:
600 Rt. 17A
Tuxedo Park, NY
View map »


Website »

More information

This festival aims to serve as a creative outlet to residents of greater New Milford by providing them with the opportunity to show their work on the big screen, all while raising money for a...

Cost: varies but mostly free

Where:
Bank Street Theater
46 Bank St
New Milford, CT
View map »


Website »

More information

Our founder, Cole Palen, grew up next to a great 1930’s Hudson Valley airport dreaming that he would own and fly the machines he saw overhead and spent the rest of his life bringing the...

Cost: $8.00 - $10.00

Where:
Old Rhinebeck Aerodrome
9 Norton Rd
Red Hook, NY
View map »


Website »

More information

Nikon Small World  exhibition runs July 29 - October 29, 2017 at Bruce Museum This exhibit showcases the top 20 award-winning photographs of the 42nd annual Nikon Small World...

Cost: $10 adult,$8 senior/student, under 5 and member free. Free on Tuesdays to all

Where:
Bruce Museum
1 Museum Drive
Greenwich, CT  06830
View map »


Sponsor: Bruce Museum
Website »

More information

Heather Gaudio Fine Art is pleased to announce “Paradigm Shifts,” a group exhibition featuring paintings by Charles Arnoldi, Ricardo Mazal and Manuel Mérida.  The show opens...

Cost: Free

Where:
Heather Gaudio Fine Art
66 Elm Street
New Canaan, CT  06840
View map »


Sponsor: Heather Gaudio Fine Art
Telephone: (203)801-9590
Contact Name: Rachael Palacios
Website »

More information

Sports and recreation are universal experiences. Whether we make it to the big leagues or never leave our backyards, these activities play important roles in our lives. They help us form...

Cost: Free!

Where:
Litchfield History Museum
7 South Street
Litchfield, CT  06759
View map »


Sponsor: Litchfield Historical Society
Telephone: 860-567-4501
Contact Name: Megan Olver
Website »

More information

The Litchfield Historical Society is pleased to announce the opening of a new exhibit Thoughts, Words, and Deeds: Exploring the Litchfield Female Academy, on view April 22 through November 27, 2017...

Cost: Free

Where:
Litchfield History Museum
7 South Street
Litchfield, CT  06759
View map »


Sponsor: Litchfield Historical Society
Telephone: 860-567-4501
Contact Name: Megan Olver
Website »

More information

The Bridge Healing Arts Center Hosts an open house for practitioners of the healing arts to explore Connecticut’s first synergistic wellness community. Providers will now be able to refer...

Cost: Free

Where:
Bridge Healing Arts Center
304 Main Street
Farmington, CT  06032
View map »


Sponsor: Bridge Healing Arts Center
Telephone: 860-710-5504
Contact Name: Vera Halina
Website »

More information

The Smithy Loft Gallery is pleased to announce a new exhibit featuring infrared photography by Litchfield, CT photographer, Wendy Costa, and contemporary drawings and paintings by Stony Creek, CT...

Cost: Free

Where:
Loft Gallery @ The Smithy Store
10 Main Street
New Preston, CT  06777
View map »


Sponsor: The Smithy Store
Telephone: 860-868-9003
Contact Name: Susan Newbury
Website »

More information

Written by Pulitzer Prize and Tony Award-winner, David Auburn (Proof), Lost Lake is an engrossing, evocative play. Part drama, part melancholy comedy, Lost...

Cost: Preview Tickets: $45; Tickets: $50

Where:
The Unicorn Stage
6 East Street
Stockbridge, MA  01262
View map »


Telephone: 413-997-4444
Website »

More information

 The Mattatuck Museum presents “The Valley Girls” with an exhibit running from September 10 – November 12, 2017.  A special reception will be held on Sunday, September...

Cost: Fee for Admission

Where:
Mattatuck Museum
144 West Main St
Waterbury, CT
View map »


Sponsor: Mattatuck Museum
Telephone: 203-753-0381
Contact Name: Mally DeSomma
Website »

More information

Show More...
Show Less...

Apple Picking Has Begun! Picking Hours: Our orchard is open daily from 9am - 4:30pm. Festival Weekends 10am - 5pm: 9/9-10 9/16-17 9/21-24 9/30-10/1 Pizza Party at...

Where:
Harvest Moon Farm & Orchard
130 Hardscrabble Road
North Salem, NY
View map »


Website »

More information

Cruise through history and the majestic beauty of the Hudson River We specialize in Weddings and Private Charters Elegance for all affairs 2 Hour narrated sightseeing cruises Customized cruises...

Cost: Adults $22 Seniors Ages 65 and up $20 Children Ages 4 to 11 $18

Where:
Hudson River Adventures, Inc
90 Front St
Newburgh, NY
View map »


Website »

More information

The Pound Ridge Historical Society will open “Modern in Pound Ridge: 20th Century Architecture + Lifestyle” at the Pound Ridge Museum on April 23, 2017. This is a real departure for the...

Cost: Free

Where:
Pound Ridge Museum
255 Westchester Ave
Pound Ridge, NY  10576
View map »


Sponsor: Pound Ridge Historical Society
Telephone: 914-764-4333
Website »

More information

Every summer, the Seaport Ferry in South Norwalk carries hundreds of hungry passengers to the historic 1868 Sheffield Island Lighthouse for the Norwalk Seaport Association's famous Thursday...

Cost: $65 or $79 per person

Where:
Sheffield Island & Lighthouse
4 North Water Street
Norwalk, CT
View map »


Website »

More information

The New Canaan Historical Society announces the opening of its exhibit Waveny – Now and Then, a celebration of the 50th anniversary of the Town’s purchase of Waveny Park.  The show...

Cost: $25/Members $35/Non-Members

Where:
The New Canaan Historical Society
13 Oenoke Ridge
13 Oenoke Rdg
New Canaan, CT  06840-4195
View map »


Sponsor: The New Canaan Historical Society
Telephone: 203-966-1776
Website »

More information

In this day of watered down comedy, Nick Di Paolo’s brutally honest performances remind us of what great stand up should be: funny, socially relevant and a little bit reckless. With Boston...

Cost: $35

Where:
The Ridgefield Playhouse
80 East Ridge Rd
Ridgefield, CT  06877
View map »


Sponsor: Barts Tree Service Comedy Series
Website »

More information

In this day of watered down comedy, Nick Di Paolo’s brutally honest performances remind us of what great stand up should be: funny, socially relevant and a little bit reckless. With Boston...

Cost: $35

Where:
Ridgefield Playhouse
80 East Ridge Road
Ridgefield, CT  06877
View map »


Sponsor: Barts Tree Service Comedy Series
Website »

More information

WCSU will present the "Best Darn Jazz Club in Danbury" at 8 p.m. in the Colonial Corner in the Student Center on the university's Midtown campus, 181 White St. in Danbury. Admission...

Cost: Free

Where:
WCSU Midtown Campus
181 White Street
Danbury, CT  06810
View map »


Website »

More information

Hilltop Hanover Farm proudly offers freshly harvested seasonal produce, herbs, and cut flowers at our farm stand. You can find your usual favorites as well as unique heirloom...

Where:
Hilltop Hanover Farm & Environmental Center
Hilltop Hanover Farm
Yorktown Heights, NY  10598
View map »


Website »

More information

Experience the joy of setting sail and shutting off the engine as we sail through Long Island Sound. Sit back and relax or take a turn at the helm, the choice is yours. Sails depart from...

Cost: $20-$40

Where:
SoundWaters
1281 Cove Rd
Stamford, CT
View map »


Website »

More information

The King of Navarre and his lords have sworn off the pleasures of life to pursue their studies, but can their oaths hold up when a princess and her ladies come to town? Men and women test their own...

Cost: $15.75-$57.75

Where:
Hudson Valley Shakespeare Festival
1601 Rt. 9D
Garrison, NY
View map »


Website »

More information

The Faire is a rollicking romp through Elizabethan England complete with 16th Century games, rides, arts, crafts, food, music and dance – set within the majestic groves of Tuxedo Park, New...

Cost: $25 for adults, $20 for military and age 62+, $12 for age 5-12, free for age 4-

Where:
600 Rt. 17A
Tuxedo Park, NY
View map »


Website »

More information

This festival aims to serve as a creative outlet to residents of greater New Milford by providing them with the opportunity to show their work on the big screen, all while raising money for a...

Cost: varies but mostly free

Where:
Bank Street Theater
46 Bank St
New Milford, CT
View map »


Website »

More information

Our founder, Cole Palen, grew up next to a great 1930’s Hudson Valley airport dreaming that he would own and fly the machines he saw overhead and spent the rest of his life bringing the...

Cost: $8.00 - $10.00

Where:
Old Rhinebeck Aerodrome
9 Norton Rd
Red Hook, NY
View map »


Website »

More information

Nikon Small World  exhibition runs July 29 - October 29, 2017 at Bruce Museum This exhibit showcases the top 20 award-winning photographs of the 42nd annual Nikon Small World...

Cost: $10 adult,$8 senior/student, under 5 and member free. Free on Tuesdays to all

Where:
Bruce Museum
1 Museum Drive
Greenwich, CT  06830
View map »


Sponsor: Bruce Museum
Website »

More information

Heather Gaudio Fine Art is pleased to announce “Paradigm Shifts,” a group exhibition featuring paintings by Charles Arnoldi, Ricardo Mazal and Manuel Mérida.  The show opens...

Cost: Free

Where:
Heather Gaudio Fine Art
66 Elm Street
New Canaan, CT  06840
View map »


Sponsor: Heather Gaudio Fine Art
Telephone: (203)801-9590
Contact Name: Rachael Palacios
Website »

More information

Sports and recreation are universal experiences. Whether we make it to the big leagues or never leave our backyards, these activities play important roles in our lives. They help us form...

Cost: Free!

Where:
Litchfield History Museum
7 South Street
Litchfield, CT  06759
View map »


Sponsor: Litchfield Historical Society
Telephone: 860-567-4501
Contact Name: Megan Olver
Website »

More information

The Litchfield Historical Society is pleased to announce the opening of a new exhibit Thoughts, Words, and Deeds: Exploring the Litchfield Female Academy, on view April 22 through November 27, 2017...

Cost: Free

Where:
Litchfield History Museum
7 South Street
Litchfield, CT  06759
View map »


Sponsor: Litchfield Historical Society
Telephone: 860-567-4501
Contact Name: Megan Olver
Website »

More information

The Smithy Loft Gallery is pleased to announce a new exhibit featuring infrared photography by Litchfield, CT photographer, Wendy Costa, and contemporary drawings and paintings by Stony Creek, CT...

Cost: Free

Where:
Loft Gallery @ The Smithy Store
10 Main Street
New Preston, CT  06777
View map »


Sponsor: The Smithy Store
Telephone: 860-868-9003
Contact Name: Susan Newbury
Website »

More information

Written by Pulitzer Prize and Tony Award-winner, David Auburn (Proof), Lost Lake is an engrossing, evocative play. Part drama, part melancholy comedy, Lost...

Cost: Preview Tickets: $45; Tickets: $50

Where:
The Unicorn Stage
6 East Street
Stockbridge, MA  01262
View map »


Telephone: 413-997-4444
Website »

More information

 The Mattatuck Museum presents “The Valley Girls” with an exhibit running from September 10 – November 12, 2017.  A special reception will be held on Sunday, September...

Cost: Fee for Admission

Where:
Mattatuck Museum
144 West Main St
Waterbury, CT
View map »


Sponsor: Mattatuck Museum
Telephone: 203-753-0381
Contact Name: Mally DeSomma
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Little Free Library Stewards Rose Buckens and Jo Ann Jaacks will host a combined indoor tag sale fundraiser and informational gathering at St. Michael’s Community House, 23 South Street, just...

Cost: Free

Where:
St. Michael's Community House
23 South Street
Just off the Litchfield Green
Litchfield, CT  06759
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Sponsor: Little Free Library at StoneHill
Telephone: 203-770-4156
Contact Name: Rose Buckens
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Apple Picking Has Begun! Picking Hours: Our orchard is open daily from 9am - 4:30pm. Festival Weekends 10am - 5pm: 9/9-10 9/16-17 9/21-24 9/30-10/1 Pizza Party at...

Where:
Harvest Moon Farm & Orchard
130 Hardscrabble Road
North Salem, NY
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The Litchfield Historical Society’s Saturday morning walking tours are exploring new sites in town. Each tour lasts about an hour—make sure to bring a bottle of water and wear...

Cost: Free for members; $5 non-members

Where:
Litchfield History Museum
7 South Street
Litchfield, CT  06759
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Sponsor: Litchfield Historical Society
Telephone: 860-567-4501
Contact Name: Megan
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Join education staff for coffee and learn more about docent opportunities at the Fairfield Museum. Docents are trained volunteer educators who present guided tours and other education programs to...

Cost: Free

Where:
Fairfield Museum and History Center
370 Beach Road
Fairfield, CT  06824
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Cruise through history and the majestic beauty of the Hudson River We specialize in Weddings and Private Charters Elegance for all affairs 2 Hour narrated sightseeing cruises Customized cruises...

Cost: Adults $22 Seniors Ages 65 and up $20 Children Ages 4 to 11 $18

Where:
Hudson River Adventures, Inc
90 Front St
Newburgh, NY
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The Pound Ridge Historical Society will open “Modern in Pound Ridge: 20th Century Architecture + Lifestyle” at the Pound Ridge Museum on April 23, 2017. This is a real departure for the...

Cost: Free

Where:
Pound Ridge Museum
255 Westchester Ave
Pound Ridge, NY  10576
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Sponsor: Pound Ridge Historical Society
Telephone: 914-764-4333
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Paul Newman and Robert Redford are Butch Cassidy and the Sundance Kid, the 1969 Western classic directed by George Roy Hill. Outlawed robbers, the two antiheros flee to Bolivia in search of a...

Cost: $7

Where:
Mahaiwe Performing Arts Center
14 Castle Street
Great Barrington, MA  01230
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Sponsor: Mahaiwe Performing Arts Center
Telephone: 413.528.0100
Contact Name: Box Office
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Larry Gatlin is the oldest of the three Gatlin brothers. By age seven, he was already accompanying younger brothers, Steve and Rudy in signing at family and church events.  On the strength of...

Cost: $37.50

Where:
The Ridgefield Playhouse
80 East Ridge Rd
Ridgefield, CT  06877
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Sponsor: Mountain Dew Country & Bluegrass Series
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Larry Gatlin is the oldest of the three Gatlin brothers. By age seven, he was already accompanying younger brothers, Steve and Rudy in singing at family and church events....

Cost: $37.50

Where:
The Ridgefield Playhouse
80 East Ridge Rd
Ridgefield, CT  06877
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Telephone: 203-438-5795
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Live From Laurel Canyon: Songs & Stories of American Folk Rock is a journey through a special time in American pop music, paying homage to the musical legacy of Laurel Canyon. A gathering of...

Cost: A: $40 B: $25

Where:
The Colonial Theatre
111 South St
Pittsfield, MA  01201
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Telephone: 413-997-4444
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Hilltop Hanover Farm proudly offers freshly harvested seasonal produce, herbs, and cut flowers at our farm stand. You can find your usual favorites as well as unique heirloom...

Where:
Hilltop Hanover Farm & Environmental Center
Hilltop Hanover Farm
Yorktown Heights, NY  10598
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Experience the joy of setting sail and shutting off the engine as we sail through Long Island Sound. Sit back and relax or take a turn at the helm, the choice is yours. Sails depart from...

Cost: $20-$40

Where:
SoundWaters
1281 Cove Rd
Stamford, CT
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The Faire is a rollicking romp through Elizabethan England complete with 16th Century games, rides, arts, crafts, food, music and dance – set within the majestic groves of Tuxedo Park, New...

Cost: $25 for adults, $20 for military and age 62+, $12 for age 5-12, free for age 4-

Where:
600 Rt. 17A
Tuxedo Park, NY
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This festival aims to serve as a creative outlet to residents of greater New Milford by providing them with the opportunity to show their work on the big screen, all while raising money for a...

Cost: varies but mostly free

Where:
Bank Street Theater
46 Bank St
New Milford, CT
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Saturdays from 9am to 1pm! For a real feel of the country drive up Rt. 22 to the John Jay Homestead where you go to market with grass under your feet, surrounded by historic buildings and...

Cost: Food prices

Where:
John Jay Homestead
400 Jay Street
Katonah, NY  10536
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Heather Gaudio Fine Art is pleased to announce “Paradigm Shifts,” a group exhibition featuring paintings by Charles Arnoldi, Ricardo Mazal and Manuel Mérida.  The show opens...

Cost: Free

Where:
Heather Gaudio Fine Art
66 Elm Street
New Canaan, CT  06840
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Sponsor: Heather Gaudio Fine Art
Telephone: (203)801-9590
Contact Name: Rachael Palacios
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Sports and recreation are universal experiences. Whether we make it to the big leagues or never leave our backyards, these activities play important roles in our lives. They help us form...

Cost: Free!

Where:
Litchfield History Museum
7 South Street
Litchfield, CT  06759
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Sponsor: Litchfield Historical Society
Telephone: 860-567-4501
Contact Name: Megan Olver
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The Litchfield Historical Society is pleased to announce the opening of a new exhibit Thoughts, Words, and Deeds: Exploring the Litchfield Female Academy, on view April 22 through November 27, 2017...

Cost: Free

Where:
Litchfield History Museum
7 South Street
Litchfield, CT  06759
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Sponsor: Litchfield Historical Society
Telephone: 860-567-4501
Contact Name: Megan Olver
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Clay Art Center’s One-Time Saturday Drop-In Clay Classes for the Whole Family Plan a great afternoon with friends, family or just yourself in this fun and messy introduction to clay for...

Cost: $20 - $30

Where:
Clay Art Center
40 Beech Street
Port Chester, NY  10573
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The Smithy Loft Gallery is pleased to announce a new exhibit featuring infrared photography by Litchfield, CT photographer, Wendy Costa, and contemporary drawings and paintings by Stony Creek, CT...

Cost: Free

Where:
Loft Gallery @ The Smithy Store
10 Main Street
New Preston, CT  06777
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Sponsor: The Smithy Store
Telephone: 860-868-9003
Contact Name: Susan Newbury
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Written by Pulitzer Prize and Tony Award-winner, David Auburn (Proof), Lost Lake is an engrossing, evocative play. Part drama, part melancholy comedy, Lost...

Cost: Preview Tickets: $45; Tickets: $50

Where:
The Unicorn Stage
6 East Street
Stockbridge, MA  01262
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Telephone: 413-997-4444
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 The Mattatuck Museum presents “The Valley Girls” with an exhibit running from September 10 – November 12, 2017.  A special reception will be held on Sunday, September...

Cost: Fee for Admission

Where:
Mattatuck Museum
144 West Main St
Waterbury, CT
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Sponsor: Mattatuck Museum
Telephone: 203-753-0381
Contact Name: Mally DeSomma
Website »

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