Festivals near Pleasant Valley, NY.

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 ....

Hudson Valley Fermentation Festival 2026

• Jun. 13 - Jun 14, 2026
• Twin Star Orchards - New Paltz, NY USA

• $1 - $10
• $10 - $25
• $25 - $50
• $50 - $100

Join us for the 2026 Hudson Valley Fermentation Festival, where you can explore a lively outdoor tasting market, packed with local producers of fermen ....

Old Mill Singers Spring Concerts: A Tapestry of American Song

• Jun. 6 - Jun 7, 2026
• The Clearview School - Briarcliff Manor, NY USA

• Music

• $10 - $25

Immerse yourself in this fabulous musical encore of the past and the evolution of today’s American music. The Old Mill Singers will perform old time ....

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 ....

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 ....

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 ....

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 ....

Spring Crafts at Lyndhurst 2026

• May. 1 - May 3, 2026
• 635 S Broadway - Tarrytown, NY USA

• $10 - $25

Westchester's favorite festival, Spring Crafts at Lyndhurst returns on May 1-3, 2026! Find handmade and uncommon items from 200 makers you can't find ....

Spring Crafts at Lyndhurst 2026

• May. 1 - May 3, 2026
• Lyndhurst Mansion - Tarrytown, NY USA

• $10 - $25

Westchester's favorite festival, Spring Crafts at Lyndhurst returns on May 1-3, 2026! Find handmade and uncommon items from 200 makers you can't find ....

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 ....

Chancellor’s Sheep and Wool Showcase

• Apr. 25 - Apr 25, 2026
• Clermont State Historic Site - Germantown, NY USA

• Other / General

• $10 - $25

The Chancellor’s Sheep and Wool Showcase is family-friendly event that features shearing demonstrations, farm animals, and historic reenactments. The ....

Charis Sings Songs of Democracy

• Apr. 24 - Apr 24, 2026
• First Presbyterian Church - New Canaan, CT USA

• Music

• $10 - $25

CHARIS SINGS SONGS OF DEMOCRACY Charis Chamber Voices celebrates America’s 250th birthday with Songs of Democracy: Friday April 24 at 7:30 p.m. at F ....

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 ....

Easter EGG-stravaganza Festival at Heaven Hill Farm

• Mar. 28 - Apr 12, 2026
• Heaven Hill Farm Garden Center and Farm Market - Vernon Township, NJ USA

• $10 - $25

HEAVEN HILL FARM/VERNON NJ: Come join in the egg-citement at Heaven Hill Farm! Our annual Easter Egg Festival is coming up, March 28th & March 29th, A ....

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 ....

17th Annual Greenwich Reindeer Festival & Santa’s Workshop

• Nov. 28 - Dec 12, 2025
• Sam Bridge Nursery & Greenhouses - Greenwich, CT USA

• Holiday (Other)
• Seasonal (Winter)

• FREE!!
• $1 - $10
• $10 - $25
• $25 - $50

17th Annual Greenwich Reindeer Festival & Santa’s Workshop presented by Jenny Allen & Kristen Studwell, Compass Real Estate at Sam Bridg ....

The Good District

• Nov. 23 - Nov 23, 2025
• The Crystal Theatre - Norwalk, CT USA

• Arts (Performing Arts)

• $10 - $25
• $25 - $50
• $50 - $100

  What do you deserve?A fractured family squats in a wealthy beachfront home to give 13-year-old Alisha a chance at a better life in an elite sc ....

The Good District - South Norwalk, November 2025

• Nov. 23 - Nov 23, 2025
• The Crystal Theatre - Norwalk, CT USA

• Arts (Performing Arts)
• Comedy Show

• $10 - $25
• $25 - $50
• $50 - $100

What do you deserve? A fractured family squats in a wealthy beachfront home to give 13-year-old Alisha a chance at a better life in anelite school. A ....

The Good District - 22 Nov 2025

• Nov. 22 - Nov 22, 2025
• The Crystal Theatre - Norwalk, CT USA

• Arts (Performing Arts)

• $10 - $25
• $25 - $50
• $50 - $100

  What do you deserve?A fractured family squats in a wealthy beachfront home to give 13-year-old Alisha a chance at a better life in an elite sc ....

The Good District - South Norwalk, November 2025

• Nov. 22 - Nov 22, 2025
• The Crystal Theatre - Norwalk, CT USA

• Arts (Performing Arts)
• Comedy Show

• $10 - $25
• $25 - $50
• $50 - $100

What do you deserve? A fractured family squats in a wealthy beachfront home to give 13-year-old Alisha a chance at a better life in anelite school. A ....

The Good District - South Norwalk, November 2025

• Nov. 21 - Nov 21, 2025
• The Crystal Theatre - Norwalk, CT USA

• Arts (Performing Arts)
• Comedy Show

• $10 - $25
• $25 - $50
• $50 - $100

What do you deserve? A fractured family squats in a wealthy beachfront home to give 13-year-old Alisha a chance at a better life in anelite school. A ....

The Good District - 21 Nov 2025

• Nov. 21 - Nov 21, 2025
• The Crystal Theatre - Norwalk, CT USA

• Arts (Performing Arts)

• $10 - $25
• $25 - $50
• $50 - $100

What do you deserve?A fractured family squats in a wealthy beachfront home to give 13-year-old Alisha a chance at a better life in an elite school. As ....

Ann's Place Festival of Trees

• Nov. 21 - Nov 23, 2025
• The Summit at Danbury - Danbury, CT USA

• $1 - $10
• $10 - $25
• $50 - $100

Ann’s Place proudly announces its 23rd Annual Festival of Trees: Honoring Hope. Celebrating courage, resilience, and community, Ann’s Place brings sup ....

The Good District - South Norwalk, November 2025

• Nov. 20 - Nov 20, 2025
• The Crystal Theatre - Norwalk, CT USA

• Arts (Performing Arts)
• Comedy Show

• $10 - $25
• $25 - $50
• $50 - $100

What do you deserve? A fractured family squats in a wealthy beachfront home to give 13-year-old Alisha a chance at a better life in anelite school. A ....