Festivals near Simsbury, 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 ....

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 ....

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 ....

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 ....

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 ....

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 ....

Mohegan Sun's Backyard Beats Music Festival coming to the Sun Patio this August!

• Aug. 16 - Aug 16, 2025
• 1 Mohegan Sun Blvd - Montville, CT USA

• Music

• $10 - $25

Backyard Beats at Mohegan Sun is bringing you a tidal wave of local talent. From high-energy Indie Rock to soulful Blues and everything in between, we ....

Jazz in the Vineyard

• Jul. 19 - Jul 19, 2025
• Millbrook Vineyards \u0026 Winery - Millbrook, NY USA

• $10 - $25

Come out to Millbrook Winery from 5:30 - 7:30 PM and enjoy an outdoor jazz concert featuring True North Jazz Project on the beautiful vineyard lawn. F ....

Jazz in the Vineyard

• Jul. 12 - Jul 12, 2025
• Millbrook Vineyards \u0026 Winery - Millbrook, NY USA

• $10 - $25

Come out to Millbrook Winery on July 12 from 5:30 - 7:30 PM and enjoy an outdoor jazz concert featuring Laura Evans & Friends on the beautiful vineyar ....

The 2025 Midsummer Fantasy Renaissance Faire

• Jun. 28 - Jul 13, 2025
• Warsaw Park - Ansonia, CT USA

• $10 - $25

?? The Midsummer Fantasy Renaissance Faire returns for its 14th season! ?? ??? June 28th & 29th, July 4th, 5th, & 6th, and July 12th & 13th 2025 Ticke ....

Summer Solstice Trail Run: 3 mile, 5 mile or 8 mile

• Jun. 21 - Jun 21, 2025
• Gay City State Park - Hebron, CT USA

• Sports / Fitness

• $10 - $25

The 3 mile loop follows the White Trail, which zig-zags through Gay City State Park. The trail starts as a wide access road with few bumps along the w ....

Close Enounters With Music: L'Amour Toujours and A World Premiere

• Jun. 8 - Jun 8, 2025
• Mahaiwe Performing Arts Center - Great Barrington, MA USA

• Arts (Performing Arts)
• Music

• $10 - $25
• $25 - $50
• $50 - $100
• $100 - $250

It's all about love: A new work for clarinet trio by composer Seth Grosshandler that celebrates young love, courtship and serendipity of meeting one's ....

Shooting the Breeze with Photojournalist Christopher Little | Talk and Book Signing

• Jun. 8 - Jun 8, 2025
• American Mural Project - Winchester, CT USA

• Arts (Book)

• $1 - $10
• $10 - $25

Shooting the Breeze-A Talk and Book Signing with Photojournalist Christopher Little Renowned photojournalist Christopher Little will share the storie ....

Savor New England

• Jun. 7 - Jun 7, 2025
• Mohegan Sun - Montville, CT USA

• Food / Wine / Beer

• $10 - $25
• $25 - $50

Savor fresh, seafood flavors and other local bites from New England restaurants*, sample all the tastes of the clam chowder competition and vote for y ....

Songs of Love at Ozawa Hall

• May. 25 - May 25, 2025
• Seiji Ozawa Hall - Lenox, MA USA

• Arts (Performing Arts)
• Music

• $10 - $25
• $25 - $50

Berkshire Choral International presents a festival chorus of 150 singers from around the U.S. under the direction of Anthony Trecek-King. Exploring so ....

CLOSE ENCOUNTERS WITH MUSIC: A TALE OF TWO SALONS - RAVEL, CEASAR FRANCK, FAURE and STRAVINSKY

• May. 18 - May 18, 2025
• Mahaiwe Performing Arts Center - Great Barrington, MA USA

• Arts (Performing Arts)
• Music

• $10 - $25
• $25 - $50
• $50 - $100

The daughter of sewing machine industrialist Isaac Merritt Singer, Winnaretta Singer-Polignac was a force of nature, hosting everyone from Leon Bakst ....

Out There: A National Parks Story

• May. 15 - May 15, 2025
• New Milford High School - New Milford, CT USA

• Community (Fundraiser)

• $10 - $25

Join us for a special screening of the award-winning feature documentary Out There: A National Parks Story in western Connecticut! The film's director ....