Festivals near Southwick, MA.

New Year’s Eve with Max Creek

• Dec. 31 - Jan 1, 2026
• The Colonial Theatre - Pittsfield, MA USA

• Music

• $25 - $50

A beloved staple of the Northeast music scene for over five decades, Max Creek defies categorization—fusing rock, country, reggae, soul, jazz and caly ....

The Wizards of Winter

• Dec. 20 - Dec 20, 2025
• The Colonial Theatre - Pittsfield, MA USA

• $50 - $100

Returning for their third year at The Colonial Theatre, The Wizards of Winter will light up the stage with The Christmas Dream—a theatrical musical jo ....

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 ....

Orleans

• Nov. 29 - Nov 29, 2025
• The Colonial Theatre - Pittsfield, MA USA

• Music

• $25 - $50

Their timeless hits—like “Still The One,” “Dance With Me,” and “Love Takes Time”—remain staples across radio, television and streaming platforms, capt ....

Classic Silent Film Night with LIVE MUSIC!

• Nov. 29 - Nov 29, 2025
• Christ Trinity Lutheran/Episcopal Church - Sheffield, MA USA

• Arts (Film / Movie / Photo)
• Arts (Performing Arts)
• Community (Community / Social)
• Community (Family & Kids)
• Music

• $10 - $25

What to do with those pesky Thanksgiving weekend guests?  Join us for a special 100th Anniversary Celebration of Charlie ....

Harvest & Rust: A Neil Young Experience

• Nov. 22 - Nov 22, 2025
• The Colonial Theatre - Pittsfield, MA USA

• Music

• $25 - $50

Western Massachusetts’ own Harvest & Rust returns to The Colonial Theatre in Pittsfield for a special tribute concert celebrating Neil Young’s 80th bi ....

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 ....

Strange Magic NY: The ELO Experience

• Nov. 8 - Nov 8, 2025
• The Colonial Theatre - Pittsfield, MA USA

• $25 - $50

Hailing from New York, this nine-piece ensemble masterfully recreates the iconic ELO sound by incorporating actual string instruments, vintage keyboar ....

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 ....

Brothers Osborne and LeAnn Rimes

• Oct. 11 - Oct 11, 2025
• Keane Stud - Amenia, NY USA

• Music

• $50 - $100

Highlands Country Night End the day with a live concert under the stars, featuring LeAnn Rimes and Brothers Osborne—a night of unforgettable country m ....

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 ....

Third Eye Blind with special guest Dinosaur Jr.

• Oct. 10 - Oct 10, 2025
• Keane Stud - Amenia, NY USA

• Music

• $50 - $100

Concert Under the Stars with Third Eye Blind Wrap up your day with a live outdoor concert by Third Eye Blind with special guest Dinosaur Jr. Bring you ....

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 ....

South Windsor Apple Fest

• Oct. 4 - Oct 4, 2025
• 75 Brookfield St - South Windsor, CT USA

Enjoy 100+ vendors and international food trucks, signature apple pie and ice cream, apple donuts, wings, adult beverages, live music including the Sa ....

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 ....

Coffee First: National Coffee Day with Cafely

• Sep. 29 - Sep 29, 2025
• Cafely - North Adams, MA USA

• FREE!!

National Coffee Day on September 29 is a cherished moment to raise a mug to the brew that fuels countless mornings, conversations, and connections acr ....

Brew Moments with Cafely This National Coffee Day

• Sep. 29 - Sep 29, 2025
• Cafely - Norwich, CT USA

• Food / Wine / Beer

• FREE!!

Hey there, coffee lover! Let’s raise a mug to National Coffee Day on September 29, a day to celebrate the rich, aromatic brew that fuels our mornings, ....

Middle Eastern Festival Sunday September 28, 2025

• Sep. 28 - Sep 28, 2025
• 341 June St - Worcester, MA USA

• Food / Wine / Beer

You don’t want to miss out on our first Middle Eastern festival scheduled for Sunday September 28. It will be a great day where the community will gat ....

Oxford Deaf Festival

• Sep. 26 - Sep 27, 2025
• Oxford Town Hall - Oxford, CT USA

Action Deafness presents Oxford Deaf Festival! Connect, Explore, and Celebrate! Join us for the Oxford Deaf Festival, an exciting event bringing tog ....

1969 BEYOND THE MUSIC

• Sep. 19 - Sep 19, 2025
• Little Theatre of Manchester at Cheney Hall - Manchester, CT USA

• $25 - $50

BEYOND 1969 highlights the best bands of 1969, including The Rolling Stones, Jimi Hendrix, and The Beatles. You'll groove to iconic hits like "Proud M ....

FreshGrass

• Sep. 19 - Sep 21, 2025
• MASS MoCA - North Adams, MA USA

• Music

• $100 - $250

Set against the foothills of the beautiful Berkshire mountains FreshGrass is a family-friendly festival with the best in bluegrass and roots music fil ....

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 ....