Festivals near Winchester, CT.

Northwest Passage - The spirit of classic Americana, the golden era of rock, blues and folk!

• May. 14 - May 14, 2026
• Buttonball Barn - Egremont, MA USA

• $10 - $25

Northwest Passage—hailing from the scenic Litchfield Hills of Northwest Connecticut—has been delighting audiences for more than a decade with their ri ....

Hugo The Ultimate Journey Tribute Concert - One night only at CT Food Truck Battles Festival

• May. 16 - May 16, 2026
• Woodtick Recreation Area - Wolcott, CT USA

• Nightlife

• $10 - $25

About the event Hugo The Ultimate Journey Tribute Concert - One night only at CT Food Truck Battles Festival The music of Journey from Hugo The Ultima ....

Hugo The Ultimate Journey Tribute Concert - One night only at CT Food Truck Battles Festival

• May. 16 - May 16, 2026
• 201 Nichols Rd - Wolcott, CT USA

• Food / Wine / Beer

• $10 - $25

2026 CT Food Truck Battles Festival - May 16, 12pm-10pm Live 80s & 90s Music all day with Special Concert Starting at 7pm HUGO The Ultimate Journey Tr ....

2026 Oxford Nature and Arts Festival

• Jun. 7 - Jun 7, 2026
• 486 Oxford Rd - Oxford, CT USA

• Other / General

On Sunday June 7, the Oxford Main Street Project Corporation will be hosting the 2026 Oxford Nature and Arts Festival. The festival will run Sunday m ....

Lee Pride Festival 2026

• Jun. 13 - Jun 13, 2026
• 18 Main St - Lee, MA USA

Building on the success of its inaugural celebration in 2025, the community of Lee and Berkshire Pride will host Lee Pride 2026 on Saturday, June 13th ....

Hudson Valley Fermentation Festival 2026

• Jun. 13 - Jun 14, 2026
• Twin Star Orchards - New Paltz, NY USA

• $1 - $10
• $10 - $25
• $25 - $50
• $50 - $100

Join us for the 2026 Hudson Valley Fermentation Festival, where you can explore a lively outdoor tasting market, packed with local producers of fermen ....

12th New Haven Caribbean Heritage Festival

• Jun. 28 - Jun 28, 2026
• 250 Temple St - New Haven, CT USA

• Other / General

Celebrate the vibrant culture, history, and traditions of the Caribbean right in the heart of the Elm City! The New Haven Caribbean Heritage Festival ....

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 ....

New Haven Chalk Art Festival

• Oct. 3 - Oct 3, 2026
• The Shops at Yale - New Haven, CT USA

• Other / General

Join us Saturday, October 3, 2026 (rain date October 4) from 12–4 p.m., as more than 60 professional and amateur artists from across Connecticut and t ....

Forage Fest: A Wild Food Gathering

• May. 9 - May 9, 2026
• (Creative Legion) - Hudson, NY USA

• Other / General

• $50 - $100

(Creative Legion) · 7 Fairview Ave, Hudson, New York Advance Tickets $75 Door Tickets $90 Talbott & Arding, Feast & Floret and (Creative Legion) br ....

Hartford Color Run By Color Craze

• May. 9 - May 9, 2026
• Hartford - Hartford, CT USA

• Community (Family & Kids)
• Health & Wellness
• Other / General
• Outdoor / Recreation
• Sports / Fitness

• $50 - $100
• $100 - $250

Welcome to Color Craze, one of the most vibrant experiences in the ColorVerse! This isn’t just a run, it’s a full-blown festival ....

Every Breath You Take: A Tribute to Sting & The Police - At ButtonBall Barn

• May. 8 - May 8, 2026
• Buttonball Barn - Egremont, MA USA

• $10 - $25

Every Breath You Take: A Tribute to Sting & The Police is more than a tribute show — it’s a high-energy, immersive celebration of one of the most infl ....

Marc Douglas Berardo & Louise Coombe - Two Acclaimed Songwriters, One Intimate Stage.

• May. 3 - May 3, 2026
• Buttonball Barn - Egremont, MA USA

• $10 - $25

Marc Douglas Berardo is a master storyteller and wooden-guitar craftsman whose songs blend humor, heart, and deep emotional resonance. A 35-year road ....

29th Annual Frog Frolic Family Festival

• May. 2 - May 3, 2026
• Redding Community Center - Redding, CT USA

• Other / General

Mark Twain’s short story, The Celebrated Jumping Frog of Calaveras County, put him on the map, jump-starting his career as the greatest American humor ....

Morgan Myles -You may know her from The Voice! Live at The BARN

• Apr. 30 - Apr 30, 2026
• Buttonball Barn - Egremont, MA USA

• $10 - $25

Morgan Myles is a powerhouse Americana and country-soul artist whose five-octave voice and raw honesty have made her one of Nashville’s most compellin ....

PLAY LIKE A GIRL; A Concert of Music by Women to Help Women

• Apr. 26 - Apr 26, 2026
• St Joseph Church - Bristol, CT USA

• Arts (Performing Arts)
• Community (Community / Social)
• Community (Fundraiser)
• Music
• Organization / Group

• FREE!!

Join us for a free concert of music composed by women to help women. The concert is free to attend, and a reception will follow. We will offer music t ....

Harugari Halfway to Oktoberfest

• Apr. 26 - Apr 26, 2026
• Harugari German-American Club - West Haven, CT USA

• Food / Wine / Beer

• $1 - $10

No need to wait until fall to celebrate—Halfway to Oktoberfest is coming at the Harugari. Join us on Sunday, April 26, beginning at noon, for an after ....

PKX Festival: Community Celebration

• Apr. 25 - Apr 25, 2026
• 45 Pershing Ave - Poughkeepsie, NY USA

A vibrant, family-friendly outdoor community celebration filled with creativity and fun for all ages! Get ready to play and create with an exciting ....

Chancellor’s Sheep and Wool Showcase

• Apr. 25 - Apr 25, 2026
• Clermont State Historic Site - Germantown, NY USA

• Other / General

• $10 - $25

The Chancellor’s Sheep and Wool Showcase is family-friendly event that features shearing demonstrations, farm animals, and historic reenactments. The ....

Woodbridge Earth Day

• Apr. 25 - Apr 25, 2026
• Woodbridge Town Green - Woodbridge, CT USA

• Other / General

This community event is hosted by the Woodbridge Ad Hoc Sustainability Committee and Town of Woodbridge. Celebrate Woodbridge Earth Day by enjoying e ....

Four Sticks - The Music of Led Zeppelin- ButtonBall Barn

• Apr. 24 - Apr 24, 2026
• Buttonball Barn - Egremont, MA USA

• $10 - $25

Few bands have defined rock & roll like Led Zeppelin—and Four Sticks brings that legendary sound roaring back to life. From the thunder of “Good Time ....

Liz Longley - Nashville-based Singer-songwriter - Live at The BARN

• Apr. 17 - Apr 17, 2026
• Buttonball Barn - Egremont, MA USA

• $25 - $50

Nashville-based Singer-songwriter Liz Longley brings an intimate and deeply moving performance to The Barn on Friday, April 17. Celebrated for her pow ....

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 ....

Cafely Just Transmits a Nimble Data Command Center

• Mar. 30 - Mar 30, 2026
• Cafely - Pleasant Valley, NY USA

• Nightlife

• FREE!!

Embark on a journey with Cafely as we delve into the pulsating heart of today’s coffee landscape, illuminated by the latest Starbucks statistics that ....

Real-Time Overviews Hub Now Live at Cafely

• Mar. 30 - Mar 30, 2026
• Cafely - West Stockbridge, MA USA

• FREE!!

Join us at Cafely as we delve into the latest Starbucks statistics and uncover the pivotal trends shaping the vibrant coffee industry of today. On Mar ....