Festivals near Winsted, CT.

The Wizards of Winter

• Dec. 20 - Dec 20, 2025
• The Colonial Theatre - Pittsfield, MA USA

• $50 - $100

Returning for their third year at The Colonial Theatre, The Wizards of Winter will light up the stage with The Christmas Dream—a theatrical musical jo ....

HUDSON VALLEY PIZZA FESTIVAL

• Dec. 13 - Dec 13, 2025
• MJN Convention Center - Mid Hudson Civic Center - Poughkeepsie, NY USA

• Food / Wine / Beer

• $25 - $50

* Unlimited Pizza Sampling with your General Admission ticket — taste the best, the cheesiest, the freshest creations from top pizza makers across the ....

Mandell JCC Book Festival: Tap Dancing on Everest

• Dec. 10 - Dec 10, 2025
• Mandell JCC - West Hartford, CT USA

• FREE!!

Part coming-of-age memoir, part adventure story, Tap Dancing on Everest is about a young medical student raised in N.Y.C., who battles self-doubt to s ....

Orleans

• Nov. 29 - Nov 29, 2025
• The Colonial Theatre - Pittsfield, MA USA

• Music

• $25 - $50

Their timeless hits—like “Still The One,” “Dance With Me,” and “Love Takes Time”—remain staples across radio, television and streaming platforms, capt ....

Classic Silent Film Night with LIVE MUSIC!

• Nov. 29 - Nov 29, 2025
• Christ Trinity Lutheran/Episcopal Church - Sheffield, MA USA

• Arts (Film / Movie / Photo)
• Arts (Performing Arts)
• Community (Community / Social)
• Community (Family & Kids)
• Music

• $10 - $25

What to do with those pesky Thanksgiving weekend guests?  Join us for a special 100th Anniversary Celebration of Charlie ....

Basilica Farm & Flea Holiday Market

• Nov. 28 - Nov 30, 2025
• Basilica Hudson - Hudson, NY USA

• Food / Wine / Beer

• $1 - $10

Born Thanksgiving Weekend 2013 as the Anti-Black Friday big sister goddess, Basilica Farm & Flea is part timeless flea market, part farmer’s market, p ....

Harvest & Rust: A Neil Young Experience

• Nov. 22 - Nov 22, 2025
• The Colonial Theatre - Pittsfield, MA USA

• Music

• $25 - $50

Western Massachusetts’ own Harvest & Rust returns to The Colonial Theatre in Pittsfield for a special tribute concert celebrating Neil Young’s 80th bi ....

Christkindlmarkt 2025!

• Nov. 21 - Nov 22, 2025
• Germania Of Poughkeepsie - Poughkeepsie, NY USA

• Other / General

A fun, festive and authentic Christkindlmarkt will be held at Germania of Poughkeepsie, 37 Old DeGarmo Road, Poughkeepsie, NY! - Friday November 21, 4 ....

Ann's Place 23rd Annual Festival of Trees

• Nov. 21 - Nov 23, 2025
• The Summit at Danbury - Danbury, CT USA

• $1 - $10

Danbury, CT – Ann’s Place proudly presents the 23rd Annual Festival of Trees: “Honoring Hope” from November 21–23, 2025 at The Summit at Danbury. Hono ....

Ann's Place Festival of Trees

• Nov. 21 - Nov 23, 2025
• The Summit at Danbury - Danbury, CT USA

• $1 - $10
• $10 - $25
• $50 - $100

Ann’s Place proudly announces its 23rd Annual Festival of Trees: Honoring Hope. Celebrating courage, resilience, and community, Ann’s Place brings sup ....

Kinderhook Reformed Church Thanksgiving Dinner Benefit

• Nov. 20 - Nov 20, 2025
• 21 Broad St - Kinderhook, NY USA

• Food / Wine / Beer

• $50 - $100

Thanksgiving meal for pick-up the day before Thanksgiving, November 26th between 2:00 and 6:00 p.m. at Kinderhook Reformed Church, 21 Broad Street, Ki ....

Dalton Country Fest

• Nov. 15 - Nov 15, 2025
• The Stationery Factory - Dalton, MA USA

• Music

• $25 - $50

Music • Dancing • Craft Fair • Food • Raffles Food will be available in the evening from Sabrina & Chin of Berkshire Flavourful Bites! Trading Post ....

Barrels For A Cause 2025

• Nov. 13 - Nov 13, 2025
• Stappa Vineyard - Orange, CT USA

• Food / Wine / Beer

• $100 - $250

Join the Rape Crisis Center of Milford & the Beth-El Center on Thursday November 13th for our 3rd annual Barrels for a Cause event at Stappa Vineyard! ....

Strange Magic NY: The ELO Experience

• Nov. 8 - Nov 8, 2025
• The Colonial Theatre - Pittsfield, MA USA

• $25 - $50

Hailing from New York, this nine-piece ensemble masterfully recreates the iconic ELO sound by incorporating actual string instruments, vintage keyboar ....

Hartford Skelly Run

• Oct. 25 - Oct 25, 2025
• Hartford - Hartford, CT USA

• Holiday (Halloween)
• Holiday (Other)
• Outdoor / Recreation
• Seasonal (Fall)
• Sports / Fitness

• $50 - $100
• $100 - $250

Get ready to lace up your running shoes for the most spine-tingling fun run of the year "Skelly Run"!Inspired by the beloved 12ft Halloween decoration ....

Connecticut Food Truck & Wine Festival

• Oct. 19 - Oct 19, 2025
• Priam Vineyards a Winiarski Family Vineyard - Colchester, CT USA

Welcome to the Connecticut Food & Wine Festival taking place on the beautiful grounds of Priam Vineyards October 18 & 19 from 11-6. This Free admissio ....

Connecticut Food Truck & Wine Festival

• Oct. 18 - Oct 18, 2025
• Priam Vineyards a Winiarski Family Vineyard - Colchester, CT USA

Welcome to the Connecticut Food & Wine Festival taking place on the beautiful grounds of Priam Vineyards October 18 & 19 from 11-6. This Free admissio ....

Brothers Osborne and LeAnn Rimes

• Oct. 11 - Oct 11, 2025
• Keane Stud - Amenia, NY USA

• Music

• $50 - $100

Highlands Country Night End the day with a live concert under the stars, featuring LeAnn Rimes and Brothers Osborne—a night of unforgettable country m ....

Eversource Hartford Marathon and Half Marathon, Charity 5K and Team 26.2 Relay

• Oct. 11 - Oct 11, 2025
• Bushnell Park - Hartford, CT USA

• Sports / Fitness

• $10 - $25

Be inspired in Hartford with a glorious start in front of the majestic Capitol. Marathon and half marathon courses venture into the welcoming neighbor ....

Third Eye Blind with special guest Dinosaur Jr.

• Oct. 10 - Oct 10, 2025
• Keane Stud - Amenia, NY USA

• Music

• $50 - $100

Concert Under the Stars with Third Eye Blind Wrap up your day with a live outdoor concert by Third Eye Blind with special guest Dinosaur Jr. Bring you ....

5th Annual Woodbridge Like Me Day

• Oct. 4 - Oct 4, 2025
• Woodbridge Town Green - Woodbridge, CT USA

Join us for the 5th Annual Woodbridge Like Me Day! Join us on Saturday, October 4 from 11 AM to 2 PM on the Woodbridge Town Green (Rain location: Am ....

South Windsor Apple Fest

• Oct. 4 - Oct 4, 2025
• 75 Brookfield St - South Windsor, CT USA

• Arts (Arts & Crafts)
• Food / Wine / Beer
• Seasonal (Fall)

• FREE!!

More than 100 crafters, international food trucks, signature apple pie and ice cream, apple donuts, wings, adult beverages, live music with New Englan ....

South Windsor Apple Fest

• Oct. 4 - Oct 4, 2025
• 75 Brookfield St - South Windsor, CT USA

Enjoy 100+ vendors and international food trucks, signature apple pie and ice cream, apple donuts, wings, adult beverages, live music including the Sa ....

Harvest Bounty German Fest

• Oct. 3 - Oct 3, 2025
• Litchfield Community Center - Litchfield, CT USA

• $1 - $10

Menu: German Food & Beer Band: Keith's Polkaparty Band * Pre-registration REQUIRED BY Wednesday Oct. 1st ....

2025 Chowder Challenge and Artisan Marketplace

• Sep. 28 - Sep 28, 2025
• Guilford Town Green - Guilford, CT USA

• $1 - $10

Join us on the Guilford Green on September 28th for the Chowder Challenge and Artisan Marketplace! From 10:00 AM to 4:00 PM, enjoy a vibrant marketpl ....