Festivals near Pawling, NY.

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 ....

Berkshire Busk!

• Jul. 3 - Sep 5, 2026
• Downtown Great Barrington - Great Barrington, MA USA

• Other / General

Our sixth season comes in three formats: BIG FESTIVAL Weekends: July 3-July 18: performances throughout Railroad Street and beyond COURTYARD Weekends: ....

Middletown 2026 Summer Concert Series

• Jul. 3 - Jul 3, 2026
• John F. Degnan Square - Middletown, NY USA

• Music

Outdoor music returns this summer at John F. Degnan Square. Join us weekly for music from 7 PM to 9 PM! ....

Parade, Picnic, Fireworks & More

• Jul. 4 - Jul 4, 2026
• Main Street South - Bethlehem, CT USA

Complete Schedule of Events: 12 Noon: Ecumenical Prayer Service – First Church of Bethlehem, 21 Main Street South. 12 - 4:30 PM: Photo Show “America ....

Friends of the C.H. Booth Library 50th Annual Book Sale

• Jul. 10 - Jul 14, 2026
• Reed Intermediate School - Newtown, CT USA

• Other / General

The 2026 sale will feature approximately 100,000 well-organized books, jigsaw puzzles, video games, CDs, DVDs and vinyl, all at our usual low prices. ....

Second Fridays at Eastdale Village

• Jul. 10 - Jul 10, 2026
• Eastdale Village Town Center - Arlington, NY USA

• Other / General

Enjoy live music by Hillbilly Parade, food from Big E BBQ and special offerings from Eastdale's shops, restaurants and businesses. Seating is availab ....

The Great Woodbridge Picnic

• Jul. 11 - Jul 11, 2026
• 4 Newton Rd - Woodbridge, CT USA

• Other / General

As communities across the country commemorate the 250th anniversary of the signing of the Declaration of Independence, Woodbridge will come together t ....

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 ....

Summerfest Free Family Carnival

• Jul. 16 - Jul 16, 2026
• Litchfield Community Center - Litchfield, CT USA

• FREE!!

Play: Hand-built, homemade carnival games like bean bag toss and bottle knockdown, run by our staff and volunteers. Eat: Carnival food, fresh popcorn ....

Summerfest Adult Splash

• Jul. 17 - Jul 17, 2026
• Litchfield Community Center - Litchfield, CT USA

• FREE!!

Who says kids get all the fun? This Adult Splash is your turn on the water slides. No lines of 8-year-olds, no cannonball contests, just you, the slid ....

Summerfest Kids Water Day!

• Jul. 17 - Jul 17, 2026
• Litchfield Community Center - Litchfield, CT USA

• FREE!!

All kids welcome What to expect: We’re turning the lawn into a water zone. Think sprinklers, water blasters, splash games, and tons of ways to cool o ....

Yonkers Waterfront Live – That Diva Band

• Jul. 17 - Jul 17, 2026
• 71 Water Grant St - Yonkers, NY USA

• Music

The Yonkers Downtown/Waterfront Business Improvement District is excited to once again bring the Yonkers waterfront to life with an exciting season of ....

Middletown 2026 Summer Concert Series

• Jul. 17 - Jul 17, 2026
• John F. Degnan Square - Middletown, NY USA

• Music

Outdoor music returns this summer at John F. Degnan Square. Join us weekly for music from 7 PM to 9 PM! ....

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 ....

Bear With Us Music Festival

• Jul. 18 - Jul 18, 2026
• Greenwood Features - Bethel, CT USA

• Music

• $25 - $50

Event Date: Saturday, July 18, 2026 Time: Doors 3:30PM / Music 4-11PM Location: Greenwood Features, 269 Greenwood Ave, Bethel, CT Join us for Bear Wi ....

Yonkers Waterfront Live – Devone Allison, BSKi, and Suzy Q

• Jul. 24 - Jul 24, 2026
• 71 Water Grant St - Yonkers, NY USA

• Music

The Yonkers Downtown/Waterfront Business Improvement District is excited to once again bring the Yonkers waterfront to life with an exciting season of ....

Middletown 2026 Summer Concert Series

• Jul. 24 - Jul 24, 2026
• John F. Degnan Square - Middletown, NY USA

• Music

Outdoor music returns this summer at John F. Degnan Square. Join us weekly for music from 7 PM to 9 PM! ....

Middletown 2026 Summer Concert Series

• Jul. 31 - Jul 31, 2026
• John F. Degnan Square - Middletown, NY USA

• Music

Outdoor music returns this summer at John F. Degnan Square. Join us weekly for music from 7 PM to 9 PM! ....

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 ....

Connecticut Country Music Festival

• Aug. 1 - Aug 1, 2026
• North Haven Fairgrounds - North Haven, CT USA

• Music

• $50 - $100

The Connecticut Country Music Festival is a one-day outdoor event featuring national and rising country artists, curated food and drink experiences, a ....

La Guelaguetza of Poughkeepsie 2026

• Aug. 2 - Aug 2, 2026
• Waryas Park Promenade - Poughkeepsie, NY USA

• Other / General

The Grupo Folclórico de Poughkeepsie and the La Guelaguetza Organizing Committee invite you to attend La Guelaguetza de Poughkeepsie 2026. La Guelague ....

Middletown 2026 Summer Concert Series

• Aug. 7 - Aug 7, 2026
• John F. Degnan Square - Middletown, NY USA

• Music

Outdoor music returns this summer at John F. Degnan Square. Join us weekly for music from 7 PM to 9 PM! ....

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 ....

Pritish Narula Live Comedy in Port Washington, New York

• Aug. 9 - Aug 9, 2026
• Jeanne Rimsky Theater - Landmark on Main Street - Port Washington, NY USA

• Comedy Show

• $25 - $50

Get ready for an unforgettable evening of laughter, sharp observations, and thought-provoking comedy as renowned stand-up comedian Pritish Narula ....

Second Fridays at Eastdale Village

• Aug. 14 - Aug 14, 2026
• Eastdale Village Town Center - Arlington, NY USA

• Other / General

Enjoy live music by Probable Cause Band, food from Frites of NY and special offerings from Eastdale's shops, restaurants and businesses. Seating is a ....