Festivals near Rhinebeck, NY.

Area 52: The Birth of a New Reality

• Jan. 31 - Jan 31, 2026
• Area 52 - Poughkeepsie, NY USA

• Music

• FREE!!

Come celebrate the launch of Area 52 What is Area 52? As I reflect on the world of weed and hemp-derived products, I find myself drawn to the innova ....

Classical Guitar: Images of Spain

• Jan. 11 - Jan 11, 2026
• Bristol Public Library - Bristol, CT USA

• Music

• FREE!!

Experience the soul of 19th century Spain in this evocative classical guitar concert, Images of Spain. The concert will feature photographs and paint ....

New Year’s Eve with Max Creek

• Dec. 31 - Jan 1, 2026
• The Colonial Theatre - Pittsfield, MA USA

• Music

• $25 - $50

A beloved staple of the Northeast music scene for over five decades, Max Creek defies categorization—fusing rock, country, reggae, soul, jazz and caly ....

The Wizards of Winter

• Dec. 20 - Dec 20, 2025
• The Colonial Theatre - Pittsfield, MA USA

• $50 - $100

Returning for their third year at The Colonial Theatre, The Wizards of Winter will light up the stage with The Christmas Dream—a theatrical musical jo ....

HUDSON VALLEY PIZZA FESTIVAL

• Dec. 13 - Dec 13, 2025
• MJN Convention Center - Mid Hudson Civic Center - Poughkeepsie, NY USA

• Food / Wine / Beer

• $25 - $50

* Unlimited Pizza Sampling with your General Admission ticket — taste the best, the cheesiest, the freshest creations from top pizza makers across the ....

Orleans

• Nov. 29 - Nov 29, 2025
• The Colonial Theatre - Pittsfield, MA USA

• Music

• $25 - $50

Their timeless hits—like “Still The One,” “Dance With Me,” and “Love Takes Time”—remain staples across radio, television and streaming platforms, capt ....

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 ....

Basilica Farm & Flea Holiday Market

• Nov. 28 - Nov 30, 2025
• Basilica Hudson - Hudson, NY USA

• Food / Wine / Beer

• $1 - $10

Born Thanksgiving Weekend 2013 as the Anti-Black Friday big sister goddess, Basilica Farm & Flea is part timeless flea market, part farmer’s market, p ....

Harvest & Rust: A Neil Young Experience

• Nov. 22 - Nov 22, 2025
• The Colonial Theatre - Pittsfield, MA USA

• Music

• $25 - $50

Western Massachusetts’ own Harvest & Rust returns to The Colonial Theatre in Pittsfield for a special tribute concert celebrating Neil Young’s 80th bi ....

Christkindlmarkt 2025!

• Nov. 21 - Nov 22, 2025
• Germania Of Poughkeepsie - Poughkeepsie, NY USA

• Other / General

A fun, festive and authentic Christkindlmarkt will be held at Germania of Poughkeepsie, 37 Old DeGarmo Road, Poughkeepsie, NY! - Friday November 21, 4 ....

Ann's Place 23rd Annual Festival of Trees

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

• $1 - $10

Danbury, CT – Ann’s Place proudly presents the 23rd Annual Festival of Trees: “Honoring Hope” from November 21–23, 2025 at The Summit at Danbury. Hono ....

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 ....

Kinderhook Reformed Church Thanksgiving Dinner Benefit

• Nov. 20 - Nov 20, 2025
• 21 Broad St - Kinderhook, NY USA

• Food / Wine / Beer

• $50 - $100

Thanksgiving meal for pick-up the day before Thanksgiving, November 26th between 2:00 and 6:00 p.m. at Kinderhook Reformed Church, 21 Broad Street, Ki ....

Thursday Organ Groove w/Conners & Doty ~ Ossining NY

• Nov. 13 - Nov 13, 2025
• Elks Lodge #1486 - Ossining, NY USA

• $1 - $10

Be our Guest and join Hammond B3 Man Paul Connors, Drummer Jon Doty and a local talent for an evening of Jazz, R&B and Blues. ....

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 ....

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 ....

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 ....

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 ....

Oxford Deaf Festival

• Sep. 26 - Sep 27, 2025
• Oxford Town Hall - Oxford, CT USA

Action Deafness presents Oxford Deaf Festival! Connect, Explore, and Celebrate! Join us for the Oxford Deaf Festival, an exciting event bringing tog ....

Allman Brothers Tribute @ Sugar Hollow Taproom

• Sep. 20 - Sep 20, 2025
• Sugar Hollow Taproom - Danbury, CT USA

• Music

• $1 - $10

This powerhouse tribute to the Allman Brothers Band has been earning rave reviews from fans and venues alike, with long time ABB fans touting Faster T ....

Music Mountain Summer Festival: 96th Season FINAL CONCERT BENEFIT - Juilliard String Quartet

• Sep. 14 - Sep 14, 2025
• Music Mountain Inc - Canaan, CT USA

• $50 - $100

Ludwig van BEETHOVEN String Quartet in A Minor, Opus 132 Antonín DVORÁK String Quintet in E Flat Major, Opus 97, "American" Tickets: $40-85, Under 19 ....

Autumn Artistry

• Sep. 14 - Sep 14, 2025
• Cunneen-Hackett Arts Center - Poughkeepsie, NY USA

Join us on Sunday, September 14, 2025, from Noon-5:00 pm for a fun and family-friendly indoor and outdoor (rain or shine) festival, “Autumn Artistry,” ....

Music Mountain Summer Festival: NEW YORK GILBERT & SULLIVAN PLAYERS

• Sep. 13 - Sep 13, 2025
• Music Mountain Inc - Canaan, CT USA

• $25 - $50

Tickets: $35-50, Under 19 Free musicmountain.org or 860-824-7126 for tickets and more information Location: Gordon Hall, Music Mountain 225 Music Mou ....

Music Brings Communities Together with Sample the Cat

• Sep. 13 - Sep 13, 2025
• Becket Arts Center - Becket, MA USA

• Music

Bring a chair, a picnic, friends or just yourself. Held outdoors on the Becket Arts Center lawn ....