Festivals near Stockbridge, MA.

Flight Night Friday: Fall Rum Punch Cocktail Flights at Bard & Baker in Troy

• Nov. 14 - Nov 14, 2025
• Bard and Baker Board Game Cafe - Troy, NY USA

Flight Night Fridays continue in 2025! Join us every Friday night 5pm-9pm as we do a different themed cocktail flight each week. Reservations aren ....

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 ....

15th Annual Mac and Cheese Bowl

• Oct. 18 - Oct 18, 2025
• Cohoes - Cohoes, NY USA

• Food / Wine / Beer

• $25 - $50

Vendors from throughout the Capital Region offer tastings of mac and cheese, with all proceeds to benefit the Regional Food Bank. ....

Regional Food Bank Mac-N-Cheese Bowl

• Oct. 18 - Oct 18, 2025
• Remsen Street - Cohoes, NY USA

• Food / Wine / Beer

• $25 - $50

Stations will span four blocks on Remsen Street where you'll be able to enjoy a sampling of each participant's recipe. VIP Tickets include a tasting f ....

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 ....

10/10/25 6pm TV Doctors (Evan Conway, Bob Morris, Josh Witmer) @ The Eleven at Lark Hall, Albany, NY

• Oct. 10 - Oct 10, 2025
• The Eleven - Albany, NY USA

• Music

Friday, October 10, 2025 6:00 pm - 8:00 pm TV Doctors (featuring: Evan Conway, Bob Morris, Josh Witmer) voted "Jam Band of the Year 2024" at The Eddie ....

Albany Skelly Run

• Oct. 4 - Oct 4, 2025
• Albany - Albany, NY 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 ....

Cider Pressing and Frost Barn Open House

• Oct. 4 - Oct 4, 2025
• Robert Frost Stone House Museum at Bennington College - Shaftsbury, VT USA

• Food / Wine / Beer

Hard cider sales and free tasting, as well as free samples of fresh-pressed juice from the Robert Frost Stone House orchard, courtesy of Watson Wheele ....

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 ....

The Arch Stanton Quartet Music Band

• Oct. 3 - Oct 3, 2025
• Opalka Gallery - Albany, NY USA

• Music

• FREE!!

The Arch Stanton Quartet Terry Gordon: Horns | Roger Noyes: Guitar | Chris Macchia: Bass | James Ketterer: Drums The Arch Stanton Quartet, based in up ....

Music from Arch Stanton Quartet

• Oct. 3 - Oct 3, 2025
• Opalka Gallery - Albany, NY USA

• Music

• FREE!!

The Arch Stanton Quartet Terry Gordon: Horns | Roger Noyes: Guitar | Chris Macchia: Bass | James Ketterer: Drums The Arch Stanton Quartet, based in ....

WHMCC's 2nd Annual Cider-Fest

• Oct. 3 - Oct 3, 2025
• 2 Museum Ln - Waterford, NY USA

• Food / Wine / Beer

• $10 - $25

With our summer programing winding down we are looking towards cooler weather and seasonal events. Please join us for our 2nd Annual Cider-Fest! We w ....

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 ....