Festivals near Winchester, CT.

Cafely Delivers Layered Insight Roast Platform

• Mar. 30 - Mar 30, 2026
• Cafely - Farmington, CT USA

• Music

• FREE!!

Join us at Cafely as we dive into the latest Starbucks statistics and uncover the pivotal trends shaping the vibrant coffee industry today. I’m thrill ....

15th Putnam County Wine & Music Fest

• Aug. 22 - Aug 23, 2026
• Putnam County Veterans Memorial Park - Carmel Hamlet, NY USA

• Music

• $10 - $25

Join us for the 15th Annual Putnam County Wine & Music Fest at Putnam County Veterans Memorial Park (Upper), 201 Gipsy Trail Road, Carmel, NY. The eve ....

WINGFEST

• Jan. 31 - Jan 31, 2026
• MJN Convention Center - Mid Hudson Civic Center - Poughkeepsie, NY USA

• Food / Wine / Beer

• $25 - $50

The renowned and famous Wingfest is returning for its 19th year! This premier wing event will take place at the spacious MJN Center in Poughkeepsie, ....

Area 52 Launch: Where Mystery Meets Innovation

• Jan. 31 - Jan 31, 2026
• American Mural Project - Winsted, CT USA

• Music

• FREE!!

Come celebrate the launch of Area 52 What is Area 52? In the realm of weed-derived products, Area 52 stands out as a beacon of quality and innovatio ....

Area 52: Explore the Unseen

• Jan. 31 - Jan 31, 2026
• Becket Athenaeum Inc - Becket, MA USA

• Music

• FREE!!

Come celebrate the launch of Area 52 What is Area 52? In the realm of hemp-derived products, Area 52 has carved out a niche for itself with a wide r ....

Area 52: The Birth of a New Reality

• Jan. 31 - Jan 31, 2026
• Area 52 - Poughkeepsie, NY USA

• Music

• FREE!!

Come celebrate the launch of Area 52 What is Area 52? As I reflect on the world of weed and hemp-derived products, I find myself drawn to the innova ....

Area 52: Step into the Multiverse

• Jan. 31 - Jan 31, 2026
• Area 52 - Plainville, CT USA

• Music

• FREE!!

Come celebrate the launch of Area 52 What is Area 52? Discover the Universe of Weed with Area 52 As I delve into the realm of weed, I find myself d ....

Classical Guitar: Images of Spain

• Jan. 11 - Jan 11, 2026
• Bristol Public Library - Bristol, CT USA

• Music

• FREE!!

Experience the soul of 19th century Spain in this evocative classical guitar concert, Images of Spain. The concert will feature photographs and paint ....

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 ....

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 ....

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! ....

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 ....

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 ....

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 ....

Music Mountain Summer Festival: 96th Season FINAL CONCERT BENEFIT - Juilliard String Quartet

• Sep. 14 - Sep 14, 2025
• Music Mountain Inc - Canaan, CT USA

• $50 - $100

Ludwig van BEETHOVEN String Quartet in A Minor, Opus 132 Antonín DVORÁK String Quintet in E Flat Major, Opus 97, "American" Tickets: $40-85, Under 19 ....

Connecticut Potato & Corn Festival

• Sep. 14 - Sep 14, 2025
• Peckham park - Middlefield, CT USA

FREE ADMISSION!! Join us in celebrating two of the tastiest foods in the world - potatoes and corn!!! Saturday September 13 from 11-7 & Sunday Septemb ....

Music Mountain Summer Festival: NEW YORK GILBERT & SULLIVAN PLAYERS

• Sep. 13 - Sep 13, 2025
• Music Mountain Inc - Canaan, CT USA

• $25 - $50

Tickets: $35-50, Under 19 Free musicmountain.org or 860-824-7126 for tickets and more information Location: Gordon Hall, Music Mountain 225 Music Mou ....