Festivals near Winchester, CT.

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 ....

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 ....

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 ....

Allman Brothers Tribute @ Sugar Hollow Taproom

• Sep. 20 - Sep 20, 2025
• Sugar Hollow Taproom - Danbury, CT USA

• Music

• $1 - $10

This powerhouse tribute to the Allman Brothers Band has been earning rave reviews from fans and venues alike, with long time ABB fans touting Faster T ....

VINYL RECORD SALE! The Windsor Record Riot! Over 10,000 LPs in one place! @Dudleytown Brewing Co

• Aug. 24 - Aug 24, 2025
• Dudleytown Brewing Company - Windsor, CT USA

• Community (Local / Fair)

• $1 - $10

It's a GIANT pop-up LP and CD event in Windsor, CT! The Record Riot is here! Sunday, August 24th at Dudleytown Brewing Company, 1001 Day Hill Road. Ov ....

BASILICA FARM & FLEA SUMMER MARKET

• Jul. 13 - Jul 13, 2025
• Basilica Hudson - Hudson, NY USA

• $1 - $10

We are thrilled to bring back the Basilica Farm & Flea Summer Market July 12th & 13th, 10am – 5pm both days. Summer Market will be jam packed with com ....

BASILICA FARM & FLEA SUMMER MARKET

• Jul. 12 - Jul 12, 2025
• Basilica Hudson - Hudson, NY USA

• $1 - $10

We are thrilled to bring back the Basilica Farm & Flea Summer Market July 12th & 13th, 10am – 5pm both days. Summer Market will be jam packed with com ....

Shooting the Breeze with Photojournalist Christopher Little | Talk and Book Signing

• Jun. 8 - Jun 8, 2025
• American Mural Project - Winchester, CT USA

• Arts (Book)

• $1 - $10
• $10 - $25

Shooting the Breeze-A Talk and Book Signing with Photojournalist Christopher Little Renowned photojournalist Christopher Little will share the storie ....

The Plainville Record Riot! Sunday June 8th! Over 10,000 vinyl records in one room!

• Jun. 8 - Jun 8, 2025
• Veterans of Foreign Wars - Plainville, CT USA

• Community (Local / Fair)

• $1 - $10

Did you just buy a turntable? The Record Riot is a PERFECT event for you. Dealers from New England and beyond will bring all sorts of musical surprise ....

Happy Hour Piano Series - Jennifer Hill

• May. 23 - May 23, 2025
• American Mural Project - Winchester, CT USA

• Arts (Performing Arts)
• Music

• $1 - $10

Fourth FridaysEach month, the Happy Hour Piano Series offers an eclectic mix of musical genres, showcasing the region’s wealth of talented piani ....

MAIFEST 2025!

• May. 16 - May 18, 2025
• Germania Festival Grounds - Poughkeepsie, NY USA

• Food / Wine / Beer
• Music

• FREE!!
• $1 - $10

GERMANIA of POUGHKEEPSIE PRESENTS: MAIFEST 2025! Germania of Poughkeepsie is sponsoring a fun, festive and authentic Maifest! The event features live ....

MAIFEST 2025!

• May. 16 - May 18, 2025
• Germania Festival Grounds - Poughkeepsie, NY USA

• FREE!!
• $1 - $10

GERMANIA of POUGHKEEPSIE PRESENTS: MAIFEST 2025! Germania of Poughkeepsie is sponsoring a fun, festive and authentic Maifest! The event features ....

CT Food Truck Battles Music, Rides and Food Festival

• May. 16 - May 18, 2025
• Woodtick Recreation Area - Wolcott, CT USA

• Other / General

• $1 - $10

Its the 4th annual Food Truck Battles which features over 50 food vendors competing for your votes on who will be crowned the 2025 greatest food truck ....

CT Food Truck Battles Music, Rides & Food Festival

• May. 16 - May 18, 2025
• 201 Nichols Rd - Wolcott, CT USA

• $1 - $10

Its the 4th annual Food Truck Battles which features over 50 food vendors competing for your votes on who will be crowned the 2025 greatest food truck ....

Cinco De Mayo Fiesta

• May. 5 - May 5, 2025
• Litchfield Community Center - Litchfield, CT USA

• Food / Wine / Beer

• $1 - $10

* Pre-registration required by Friday, May 2. REGISTER ¡Celebrate Cinco de Mayo in style! Join us for an unforgettable Cinco de Mayo fiesta filled w ....

GIANT VINYL RECORD SALE! The Plainville Record Riot! Sunday April 13th!

• Apr. 13 - Apr 13, 2025
• Veterans of Foreign Wars - Plainville, CT USA

• Community (Local / Fair)

• $1 - $10

Did you just buy a turntable? The Record Riot is a PERFECT event for you. Dealers from New England and beyond will bring all sorts of musical surprise ....

"Rock and Bowl" Fundraiser for South Community Food Pantry

• Apr. 11 - Apr 11, 2025
• Masonic Lodge - Pittsfield, MA USA

• Community (Fundraiser)

• $1 - $10
• $10 - $25
• $50 - $100

South Community Food Pantry is the largest food pantry in Berkshire County, providing free food and hot meals to over 1,000 families each week. It is ....

The WPKN Music Mash 2025! A vinyl record show to support 89.5 WPKN-FM. Saturday March 29th

• Mar. 29 - Mar 29, 2025
• Foolproof Brewing Company - BRIDGEPORT - Bridgeport, CT USA

• Community (Fundraiser)
• Community (Local / Fair)

• $1 - $10
• $10 - $25

What is Music Mash 2025? It's a dynamic Record Fair by WPKN 89.5-FM with 40+ tables featuring vinyl LPs, 45s, CDs, and music collectibles from dealers ....

BIG VINYL RECORD SALE! Enfield Record Riot! Sun March 16th @Enfield American Legion 9:30 AM-3:30 PM

• Mar. 16 - Mar 16, 2025
• American Legion - Enfield, CT USA

• Community (Local / Fair)

• $1 - $10
• $10 - $25

DUST OFF YOUR TURNTABLE! The Enfield Record Riot is BACK! @The American Legion, 566 Enfield Street. Dealers from New England and beyond will bring all ....

Incognito Witch the Musical

• Mar. 8 - Mar 8, 2025
• Becket Arts Center - Becket, MA USA

• Arts (Performing Arts)

• $1 - $10
• $10 - $25

Incognito Witch The Musical is a quirky magical-realism dramedy following G the Incognito Witch, an artist navigating life after a tumultuous divorce. ....

Family Day

• Mar. 8 - Mar 8, 2025
• American Mural Project - Winchester, CT USA

• Other / General

• $1 - $10
• $10 - $25

Looking for creative, engaging activities for the whole family? AMP's Family Days offer an exciting lineup of hands-on activities for children of all ....

Happy Hour Piano Series - Garnell Curtis

• Feb. 28 - Feb 28, 2025
• American Mural Project - Winchester, CT USA

• Arts (Performing Arts)
• Music

• $1 - $10

Garnell Curtis is a dynamic pianist known for his improvisational flair and ability to defy categorization. He's no stranger to jazz, classical, soul, ....