Festivals near Winsted, CT.

Parade, Picnic, Fireworks & More

• Jul. 4 - Jul 4, 2026
• Main Street South - Bethlehem, CT USA

Complete Schedule of Events: 12 Noon: Ecumenical Prayer Service – First Church of Bethlehem, 21 Main Street South. 12 - 4:30 PM: Photo Show “America ....

Berkshire Busk!

• Jul. 3 - Sep 5, 2026
• Downtown Great Barrington - Great Barrington, MA USA

• Other / General

Our sixth season comes in three formats: BIG FESTIVAL Weekends: July 3-July 18: performances throughout Railroad Street and beyond COURTYARD Weekends: ....

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 ....

Create A Castle Live Sculptor Demonstration & Interactive Station During Raspberry Festival

• Jun. 27 - Jun 27, 2026
• Lyman Orchards Apple Barrel Farm Market - Middlefield, CT USA

• Other / General

Create A Castle is a local family business and Shark Tank success story that revolutionized sandcastle building with its patented Split Mold technolog ....

Raspberry Festival

• Jun. 27 - Jun 27, 2026
• Lyman Orchards Apple Barrel Farm Market - Middlefield, CT USA

• Other / General

Save the Date! Continue to check back as we add more activities! The Lyman Orchards Raspberry Festival celebrates raspberry season with some fun for t ....

Blandford's Happy Birthday America 250 Celebration

• Jun. 26 - Jun 27, 2026
• Fairgrounds - Blandford, MA USA

FRIDAY NIGHT FIREWORKS & FUN – FRIDAY, JUNE 26, 2026 6PM–9:30PM at the Blandford Fairgrounds • LIVE MUSIC – The Pitoniak Brothers • FIREWORKS – After ....

TurnPark Summer Festival: Myth

• Jun. 13 - Jun 13, 2026
• TurnPark Art Space - West Stockbridge, MA USA

• Other / General

• $25 - $50

The Annual TurnPark Summer Festival returns on June 13th, 2026, under the theme “Myth”! We invite you to join us for another summer day filled with p ....

PAWPAWPALOOZA 2026

• Jun. 13 - Jun 13, 2026
• 94 S Main St - Newtown, CT USA

Join us for our 5th Annual pet adoption and open house on Saturday, June 13th from 11AM–3PM at Pleasant Paws Pet Center in Newtown, CT! PAWPAWPALOOZA ....

Strawberry Festival

• Jun. 13 - Jun 13, 2026
• Lyman Orchards Apple Barrel Farm Market - Middlefield, CT USA

• Other / General

It’s all happening at the Apple Barrel Farm Market and grounds on Saturday, June 13th, 10 AM - 4 PM! Activities (subject to change, stay tuned as we a ....

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 ....

Music Mountains 97th Season Opening Benefit Concert & Reception Feat. Benjamin Hochman & Friends

• Jun. 7 - Jun 7, 2026
• 225 Music Mountain Rd - Canaan, CT USA

• Music

• $50 - $100

Benjamin Hochman & Friends from the Met Opera Benjamin Hochman, Piano Benjamin Bowman, Violin Milan Milisavljevic, Viola Joel Noyes, Cello Johann Seb ....

Spring Art Walk Returns to Historic Lenox Village June 6 & 7

• Jun. 7 - Jun 7, 2026
• Lenox Historic Village - Lenox, MA USA

• Other / General

On Saturday, June 6 and Sunday, June 7, the town of Lenox will host the 2026 Spring Art Walk. The event is a collaboration between the Lenox Chamber o ....

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 ....

Blue Rider Stables Summer Benefit

• Jun. 6 - Jun 6, 2026
• 15 Farm Ln - Great Barrington, MA USA

• Music

• $50 - $100

This annual event brings together supporters, families, riders and friends for an evening of equines, celebration, and live music, in support of Blue ....

Berkshire Bach Society presents MUSIK VOR BACH: 17th CENTURY FRENCH AIRS DE COUR

• Jun. 6 - Jun 6, 2026
• Unitarian Universalist Meeting of South Berkshire - Housatonic, MA USA

• Music

• $25 - $50

Berkshire Bach presents MUSIK VOR BACH: 17th century FRENCH AIRS DE COUR, a concert of early Baroque music featuring James Reese, tenor, and Brandon ....

Spring Art Walk Returns to Historic Lenox Village June 6 & 7

• Jun. 6 - Jun 6, 2026
• Lenox Historic Village - Lenox, MA USA

• Other / General

On Saturday, June 6 and Sunday, June 7, the town of Lenox will host the 2026 Spring Art Walk. The event is a collaboration between the Lenox Chamber o ....

June 5 First Fridays at Five

• Jun. 5 - Jun 5, 2026
• Pittsfield - Pittsfield, MA USA

• Other / General

June 5 First Fridays at Five The City of Pittsfield, Downtown Pittsfield, Inc. (DPI), and the Downtown Pittsfield Cultural Association (DPCA) have a ....

2026 Town of Cromwell Farmers Market

• Jun. 5 - Sep 4, 2026
• 1 River Rd - Cromwell, CT USA

• Food / Wine / Beer

The beautiful Riverport Park is conveniently located on the Connecticut River at the junction of Route 9. The Town of Cromwell Farmers Market is dedic ....

2026 Town of Cromwell Farmers Maret

• Jun. 5 - Sep 4, 2026
• 1 River Rd - Cromwell, CT USA

• Food / Wine / Beer

The beautiful Riverport Park is conveniently located on the Connecticut River at the junction of Route 9. The Town of Cromwell Farmers Market is dedic ....

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 ....

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 ....

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 ....