Curated by creative producer Cat Henry and hosted by jazz media personality Keanna Faircloth, the festival invites audiences to experience fall in the Hudson Valley with a dynamic lineup of jazz’s most exciting rising stars—including Joel Ross, Julius Rodriguez, Caity Gyorgy, and BIGYUKI—in one of the region’s most beautiful and walkable small towns.

Celebrate the opening of the Mahaiwe’s flexible new performance space the Indigo Room! Events include a stand-up comedy night headlined by Kevin McCaffrey with host Thomas Attila Lewis and multiple supporting comedians on 10/10 at 7pm followed by drag bingo with Miranda Moirai on 10/10 at 9:30pm, jazz and pop singer Ann Hampton Callaway on 10/11 at 8pm; a free family-friendly concert by children’s performer Terry a La Berry on 10/12 at 11am; and blues musician Guy Davis on on 10/12 at 8pm.

Enjoy live music from Mama Train, hors d'oeuvres, desserts and drinks, all for only $35 at the door or $30 prepaid. Many artists will be available to discuss their work.

Berkshire Museum and the Berkshire County Historical Society are proud to present a FREE all-ages event.
Celebrate the season with a variety of crafts, games and hands-on activities for children and adults to enjoy.

A combination comedy show and wine tasting. A one-of-a-kind comedy and wine pairing event that’s as fun for your palate as it is for your funny bone. Four comedians, four wines, one unforgettable night.

Over 75 local artists will have their work for sale over two weekends at the historic 1842 Merwinsville Hotel. Fine art and photography, jewelry, fused glass, woodworking, fiber arts, and other fine crafts! A portion of all sales benefits the restoration of this historic railroad hotel.

A combination comedy show and wine tasting. A one-of-a-kind comedy and wine pairing event that’s as fun for your palate as it is for your funny bone. Four comedians, four wines, one unforgettable night.

Over 75 local artists will have their work for sale over two weekends at the historic 1842 Merwinsville Hotel. Fine art and photography, jewelry, fused glass, woodworking, fiber arts, and other fine crafts! A portion of all sales benefits the restoration of this historic railroad hotel.

Puremovement American Street Dance Theater. Celebrated choreographer Rennie Harris lays down his three laws of hip-hop—individuality, creativity, innovation.

Latin American Instruments on a Musical Heritage Journey
Explore South America’s colonial music through a blend of indigenous, European, and African musical elements. This unique ensemble will present transcriptions and arrangements of early compositions and folk themes, alongside contemporary fusion pieces by composers and artists such as Manuel de Zumaya, Antonio Sarrier, Illapu, and Los Kjarkas.
October 18 4PM @ Saint James Place Great Barrington MA
October 19 4PM @ Trinity Lime Rock, Lakeville CT

A book signing with Frances Palmer, in celebration of the release of her second book, Life with Flowers: Inspiration and Lessons from the Garden.

This year features a garden of ghostly night-blooming paper flowers and animatronic moths by Rhonda Weppler, a stuffed animal shrine with a dark secret by Ben Pinder, a decaying digital archive inhabited by forgotten signals and corrupted memories from misfiring information media by Amarildo Moraes and more...

Pop and R&B singer Matt Cusson performing at the Indigo Room!

A Doll's House, Part 2 by Lucas Hnath
FREE Play Readings by Connecticut Theater Exchange
Sponsored by The Judy Black Memorial Park and Gardens.
Saturday, Oct 25, 2025 at 6PM
Sunday, Oct 26, 2025 at 3PM
Advanced registration is required.

Drop off: Bring your pre-carved or pre-painted pumpkins to The Judy Black Park in Washington Depot, CT by 10AM
Voting: 10AM-12PM; the public is invited to cast ballot!
Winners Announced: 12:30PM.

Artist Patricia Avellan's second exhibition at the park, “Process."
Opening reception is free and open to the public.

Experience a compelling reimagining of Silkroad’s acclaimed ‘American Railroad’ program—now with an intimate, powerhouse ensemble of eight world-class musicians led by the internationally acclaimed pipa master, Wu Man.

In James Turrell’s hands, light is more than simply a source of illumination: it is a discrete, physical object. His sculptures and architectural interventions elevate our experience and perception of light and space.

Amy Podmore is propelled by an interest in surrealist strategies of transformation and the line between stillness and motion in sculpture.

Rockwell, Wyeth, and Parrish from the Edison. A rare series of early twentieth century lighting advertisements by Norman Rockwell and fellow Golden Age illustrators.created for Edison Mazda Lamps, a division of the General Electric Company.

Mariel Capanna (b. 1988, Philadelphia, where she lives and works) plays what she calls “games of remembering” as a way of reckoning with loss. Working from home videos and family slideshow, the artist races to record fleeting memory images in oil paint. Opening lecture on 2/15 and special event on 5/17.

The exhibit celebrates the important role of French’s female models, alongside the works of Evelyn Beatrice Longman and Margaret French Cresson, two artists who were active at Chesterwood. Sculptures and paintings—many never before exhibited—to explore themes of collaboration and mentorship.

Vincent Valdez bears witness to the world around him, chronicling America at the margins. Just a Dream… is the artist’s first major museum survey including work from over twenty years across all media.

Katrina Majkut is an American Ukrainian artist working in New York. Majkut works in cross stitch, paint and other media to create artwork with a strong feminist voice and message. Her work includes images of objects used in obstetrics, sex education, and often depicts sports figures and early female explorers.
Opening Reception: September 13, 4 - 6 pm, public invited

An art exhibition, “Easier Said Than Done: From Inspiration to Resolution,” featuring the works of Frank Greco.
Opening reception Saturday, September 27 from 3-5PM. This event is free and open to the public.

Step into the intrigue of Agatha Christie's legendary whodunit that has captivated audiences for over 70 years! When a snowstorm traps a group of strangers in a remote manor, secrets unravel, tensions rise and murder lurks in the shadows. With every character a suspect and twists around every corner, can you solve the mystery before the final curtain falls?

The Good Gallery are exited to share the work of well know local Artisan Greg St.John. St.John mentions “the featured works are inspired by evening walks through the neighborhood and portray the changing surroundings and landscape through seasons”.

Eric Forstmann’s 25th annual one-man show. We celebrate a quarter of a century representing this artist. The show will feature new works from the artist as well as works throughout his career. The gallery is open Mon, Wed, Thurs, Fri & Sat from 10 am - 5 pm.
Artist’s reception Saturday, October 11, 2025, from 3-6PM.

Final three days of the 38th Annual Autumn Arts & Fine Craft Show. Over 75 local artists will have their work for sale over at the historic 1842 Merwinsville Hotel. Fine art and photography, jewelry, fused glass, woodworking, fiber arts, and other fine crafts! A portion of all sales benefits the restoration of this historic railroad hotel.

The Judy Black Memorial Park and Gardens is pleased to welcome back artist Patricia Avellan for her second exhibition at the park, “Process.” Check our social media for weekly open hours: @judyblackpark on Instagram and Facebook.