Festivals near Canaan, CT.

New Haven Chalk Art Festival

• Oct. 3 - Oct 3, 2026
• The Shops at Yale - New Haven, CT USA

• Other / General

Join us Saturday, October 3, 2026 (rain date October 4) from 12–4 p.m., as more than 60 professional and amateur artists from across Connecticut and t ....

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 ....

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 ....

Hartford Color Run By Color Craze

• May. 9 - May 9, 2026
• Hartford - Hartford, CT USA

• Community (Family & Kids)
• Health & Wellness
• Other / General
• Outdoor / Recreation
• Sports / Fitness

• $50 - $100
• $100 - $250

Welcome to Color Craze, one of the most vibrant experiences in the ColorVerse! This isn’t just a run, it’s a full-blown festival ....

Forage Fest: A Wild Food Gathering

• May. 9 - May 9, 2026
• (Creative Legion) - Hudson, NY USA

• Other / General

• $50 - $100

(Creative Legion) · 7 Fairview Ave, Hudson, New York Advance Tickets $75 Door Tickets $90 Talbott & Arding, Feast & Floret and (Creative Legion) br ....

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 ....

29th Annual Frog Frolic Family Festival

• May. 2 - May 3, 2026
• Redding Community Center - Redding, CT USA

• Other / General

Mark Twain’s short story, The Celebrated Jumping Frog of Calaveras County, put him on the map, jump-starting his career as the greatest American humor ....

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 ....

PLAY LIKE A GIRL; A Concert of Music by Women to Help Women

• Apr. 26 - Apr 26, 2026
• St Joseph Church - Bristol, CT USA

• Arts (Performing Arts)
• Community (Community / Social)
• Community (Fundraiser)
• Music
• Organization / Group

• FREE!!

Join us for a free concert of music composed by women to help women. The concert is free to attend, and a reception will follow. We will offer music t ....

Harugari Halfway to Oktoberfest

• Apr. 26 - Apr 26, 2026
• Harugari German-American Club - West Haven, CT USA

• Food / Wine / Beer

• $1 - $10

No need to wait until fall to celebrate—Halfway to Oktoberfest is coming at the Harugari. Join us on Sunday, April 26, beginning at noon, for an after ....

PKX Festival: Community Celebration

• Apr. 25 - Apr 25, 2026
• 45 Pershing Ave - Poughkeepsie, NY USA

A vibrant, family-friendly outdoor community celebration filled with creativity and fun for all ages! Get ready to play and create with an exciting ....

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 ....

Woodbridge Earth Day

• Apr. 25 - Apr 25, 2026
• Woodbridge Town Green - Woodbridge, CT USA

• Other / General

This community event is hosted by the Woodbridge Ad Hoc Sustainability Committee and Town of Woodbridge. Celebrate Woodbridge Earth Day by enjoying e ....

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 ....

Liz Longley - Nashville-based Singer-songwriter - Live at The BARN

• Apr. 17 - Apr 17, 2026
• Buttonball Barn - Egremont, MA USA

• $25 - $50

Nashville-based Singer-songwriter Liz Longley brings an intimate and deeply moving performance to The Barn on Friday, April 17. Celebrated for her pow ....

Cafely Just Transmits a Nimble Data Command Center

• Mar. 30 - Mar 30, 2026
• Cafely - Pleasant Valley, NY USA

• Nightlife

• FREE!!

Embark on a journey with Cafely as we delve into the pulsating heart of today’s coffee landscape, illuminated by the latest Starbucks statistics that ....

Real-Time Overviews Hub Now Live at Cafely

• Mar. 30 - Mar 30, 2026
• Cafely - West Stockbridge, MA USA

• FREE!!

Join us at Cafely as we delve into the latest Starbucks statistics and uncover the pivotal trends shaping the vibrant coffee industry of today. On Mar ....

Cafely Just Instigates a Detailed PerkStats Engine

• Mar. 30 - Mar 30, 2026
• Cafely - Great Barrington, MA USA

• FREE!!

Join Cafely to dive into the latest Starbucks statistics and uncover the pivotal trends shaping today’s vibrant coffee industry. In a world where coff ....

Cafely Delivers Layered Insight Roast Platform

• Mar. 30 - Mar 30, 2026
• Cafely - Farmington, CT USA

• Music

• FREE!!

Join us at Cafely as we dive into the latest Starbucks statistics and uncover the pivotal trends shaping the vibrant coffee industry today. I’m thrill ....

WINGFEST

• Jan. 31 - Jan 31, 2026
• MJN Convention Center - Mid Hudson Civic Center - Poughkeepsie, NY USA

• Food / Wine / Beer

• $25 - $50

The renowned and famous Wingfest is returning for its 19th year! This premier wing event will take place at the spacious MJN Center in Poughkeepsie, ....

Area 52 Launch: Where Mystery Meets Innovation

• Jan. 31 - Jan 31, 2026
• American Mural Project - Winsted, CT USA

• Music

• FREE!!

Come celebrate the launch of Area 52 What is Area 52? In the realm of weed-derived products, Area 52 stands out as a beacon of quality and innovatio ....

Area 52: Explore the Unseen

• Jan. 31 - Jan 31, 2026
• Becket Athenaeum Inc - Becket, MA USA

• Music

• FREE!!

Come celebrate the launch of Area 52 What is Area 52? In the realm of hemp-derived products, Area 52 has carved out a niche for itself with a wide r ....