Festivals near Winsted, CT.

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 ....

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 ....

Yidstock: The Festival of New Yiddish Music

• Jul. 9 - Jul 12, 2026
• Yiddish Book Center - Amherst, MA USA

• $25 - $50

Join us for Yidstock: The Festival of New Yiddish Music, the Yiddish Book Center’s annual celebration of klezmer and contemporary Yiddish music in Amh ....

Summerfest Free Bubble Show

• Jul. 14 - Jul 14, 2026
• Litchfield Community Center - Litchfield, CT USA

• FREE!!

Bubbletastic Bubble Show with Charlie and the Bubble Factory All ages Watch in amazement as Charlie and the Bubble Factory transform soap and air in ....

Blueberry Festival

• Jul. 18 - Jul 18, 2026
• Lyman Orchards Apple Barrel Farm Market - Middlefield, CT USA

• Other / General

SAVE THE DATE! Lyman Orchards Blueberry Festival will be at the Apple Barrel Farm Market on Saturday, July 18th, 10 AM - 4 PM! Activities (Subject to ....

Community Read: Renegade Revolutionary (Gen. Charles Lee) & Author Talk with Dr. Phillip Papa

• Jul. 18 - Jul 18, 2026
• Lee Library - Lee, MA USA

Community Read: Renegade Revolutionary - The Life of General Charles Lee & Author Talk with Dr. Phillip Papas Date & Time: Reading Series: May 28 – J ....

Sunflower Maze Opening Day Celebration

• Aug. 1 - Aug 1, 2026
• Lyman Orchards Sunflower Maze - Middlefield, CT USA

• Other / General

• $10 - $25

The Sunflower Maze at Lyman Orchards will be opening Saturday, August 1st at 9 AM! Celebrate with some fun for the whole family at the Apple Barrel Fa ....

Peach Festival

• Aug. 8 - Aug 8, 2026
• Lyman Orchards Apple Barrel Farm Market - Middlefield, CT USA

• Other / General

Activities (Subject to change, stay tuned as we add more!): 8 AM - 4:30 PM: Pick Your Own Peaches, Apples & Pears available, located on South Street ....

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 ....

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 ....