2025 Fall Arts and Events Guide

Autumn has the RI region bursting with color, and things to do and see. As the leaves turn, our towns come alive with festivals, performances, and seasonal traditions. From outdoor art happenings and harvest fairs to world-class concerts and quirky small-town celebrations, the fall of 2025 offers a nearly endless selection of attractions. Here’s a curated guide to the major events this season.

Festivals & Fairs

69th Annual Fall Foliage Parade

Now-October 5, 1pm, Main Street, North Adams, MA

North Adams’s signature fall parade marches on with a cosmic twist this year. Floats, marching bands, and costumed revelers will embrace the theme “To Northern Berkshire & Beyond,” decking out the 1.2-mile route with playful galactic decor. Expect everything from homemade “planets” orbiting on floats to kids dressed as astronauts and aliens. This beloved community parade has celebrated autumn in the Berkshires for nearly seven decades, drawing families from across the region to Main Street for a festive afternoon. Arrive early to snag a good viewing spot.

Hudson Jazz Festival

October 3-5, Hudson, NY

The Hudson Jazz Festival returns to Hudson with three days of virtuosic jazz across multiple venues. Curated by Cat Henry, it features top talent like pianist Julius Rodriguez and vocalist Caity Gyorgy among others. Many performances center around Hudson Hall, which hosts the festival, but free pop-up sets along Warren Street add to a citywide celebratory feel. Whether you catch one show or immerse yourself all weekend, this festival swings with the creative energy of international jazz.

Chatham OctoberFeast

October 4, Main Street, Chatham, NY

The village of Chatham throws a charming all-day fall street festival each year. OctoberFeast fills Main Street with seasonal food and drink, local artisans, hay rides, and live music. Don’t miss the costumed dog parade or the carved pumpkin contest showcasing creative jack-o’-lanterns along the sidewalks. It’s a free, family-friendly celebration of small-town autumn, complete with the aromas of cider doughnuts and harvest soup in the air. Festivities run from late morning to late afternoon.

Handcrafted Octoberfest

October 4-5, Dutchess County Fairgrounds, Rhinebeck, NY

Part craft show, part Oktoberfest, this weekend extravaganza at the Dutchess County Fairgrounds offers the best of both worlds. Over 100 artisans showcase handmade jewelry, pottery, fiber arts, woodwork and more, while the fairgrounds also host pumpkin painting, hayrides, a petting zoo, and giant pumpkin weigh-offs. Sip local craft beer or cider in the brew garden and enjoy live music ranging from blues to retro rock throughout the day. The festivities go down rain or shine. Tickets are $13 and cover both days.

Berkshire Scenic Railway Fall Foliage Trains

October 4, 5, 11-13 18, 19, Adams Station, 3 Hoosac St, Adams, MA

Experience the autumn colors of the Berkshires by vintage train. On Saturdays, the Berkshire Scenic Railway runs one-hour round-trip rides through the Hoosac Valley from Adams Station, using 1950s rail cars behind a classic diesel locomotive. Passengers can opt for standard coach or upgrade to a first-class car (a restored 1956 “Daylight Speedliner” with plush reclining seats and panoramic views). It’s a leisurely, nostalgic journey past rolling hills and historic mill towns, often with a guide sharing local history. Trains depart around 1:30pm and tickets often sell out—so reserve ahead for this leaf-peeping adventure.

68th Salisbury Fall Festival

October 11-12, 2025, Main Street, Salisbury & Lakeville, CT

For Columbus Day weekend, twin villages Salisbury and Lakeville welcome visitors to a picture-perfect New England fall festival. The hallmark is a colorful Scarecrow Contest: handcrafted scarecrows created by locals line Main Street, turning the town into an outdoor gallery of spooky and silly characters. Throughout the weekend you’ll find live music, a craft fair on the green, seasonal foods (think pumpkin pancake breakfasts and cider doughnuts), hayrides to local farms, and kid-friendly fun like face painting and pumpkin decorating. Shops offer sidewalk sales and autumn specials, and foliage typically peaks in early October to provide a stunning backdrop.

Berkshire Botanical Garden Harvest Festival

October 11-12, Berkshire Botanical Garden, Stockbridge, MA

Now in its 85th year, the Harvest Festival transforms the garden’s 24-acre grounds into a country fair with over 80 artisan and farm vendors selling crafts, plants, and produce. Enjoy live folk and bluegrass music as you browse handmade pottery and lots of other local goods, then refuel at food trucks. Kids can romp through a hay maze, hitch a hayride, or join a pumpkin decorating session. Garden staff also host a huge plant sale and fun extras like a greenhouse treasure hunt. Modest admission fees support the nonprofit.

Connecticut Garlic & Harvest Festival

October 11-12, Bethlehem Fairgrounds, Bethlehem, CT

Garlic lovers unite in Bethlehem for a one-of-a-kind harvest festival that vampires hate! At the Bethlehem Fairgrounds you can sample garlicky foods both gourmet and eccentric, from garlic dips and oils to garlic ice cream and fried garlic cloves. Dozens of vendors offer garlic bulbs (many heirloom varieties) and other farm produce amidst cooking demos and gardening talks on growing your own garlic. Live music and carnival games keep the atmosphere lively, and there’s plenty for kids to do as well.

New York State Sheep & Wool Festival

October 18-19, Dutchess County Fairgrounds, Rhinebeck, NY

One of the nation’s most famous fiber festivals, New York State Sheep & Wool draws thousands of knitters and fiber artists to the Dutchess County Fairgrounds. Barns brim with sheep, alpacas, llamas, and angora rabbits (with judging competitions for each), while over 200 vendors sell every imaginable yarn, fleece, and woolen craft. Attendees often show off their own hand-knit creations, turning the fairgrounds into a cozy fashion parade of sweaters and shawls. Even if you don’t knit, there’s fun to be had: Pet an alpaca, watch sheep-shearing and herding demos, and cheer on the famous leaping llamas obstacle course. Indulge in lamb barbecue or apple cider doughnuts between browsing. After nearly 40 years, the Sheep & Wool Festival is a Hudson Valley fall institution. (tickets are $12 at the gate.

Falls Village Fall Festival

October 18, Town Green, Falls Village, CT

This little town throws a down-home fall festival that’s big on charm. For one afternoon, the town green becomes a hub of classic country fun, including hayrides through the pumpkin patch, a pie-baking contest, and live folk music. Local cooks serve chili and burgers courtesy of the volunteer fire department, while kids play old-time games like sack races and try their hand at stuffing scarecrows. It’s free to attend and a perfect add-on if you’re leaf-peeping or visiting nearby attractions.

Stage & Screen

“Metamorphoses”

Now-October 26, Unicorn Theatre, 6 East St, Stockbridge, MA

Berkshire Theatre Group presents Mary Zimmerman’s acclaimed play “Metamorphoses,” which artfully adapts Ovid’s classical myths on stage around a pool of water. In the Unicorn Theatre’s intimate space, gods and mortals enact timeless tales with actors wading and even submerging in water to create dreamlike imagery. With just 122 seats, audiences are almost within arm’s reach of the splashing and drama, making for an immersive theatrical experience. Consider booking ahead for a chance to be transported by this visually magical production.

Celebrating Jewish Plays – Staged Reading Festival

October 10-12, Elayne P. Bernstein Theatre, Lenox, MA

Shakespeare & Company shines a spotlight on Jewish playwrights this fall with a special weekend of staged readings. Over three days, audiences can hear four acclaimed plays in intimate readings: classics like Arthur Miller’s “The Price” and Wendy Wasserstein’s “The Sisters Rosensweig, a recent Holocaust-themed docudrama “Here There Are Blueberries,” and Karen Hartman’s poignant “Roz & Ray.” The cast includes Tony nominee John Douglas Thompson. With minimal sets and scripts in hand, the focus is on powerful writing and performance, often followed by talkbacks that invite deeper discussion. Whether you attend one or all four readings at the cozy Elayne P. Bernstein Theatre, you’ll experience thought-provoking theater in the heart of the Berkshires.

“The Weekend” – World Premiere at Barrington Stage

Now-October 12, St. Germain Stage, Pittsfield, MA

Be among the first to see a brand-new dramedy premiering at Barrington Stage Company. “The Weekend,” by Ben Diskant, follows a couple’s attempt at a romantic lakeside getaway that gets upended when an oblivious brother shows up uninvited. The intimate three-character play finds humor and heart in the chaos that ensues, exploring how people reassess life and relationships when plans go awry. Directed by Alan Paul, this production continues Barrington Stage’s tradition of developing new works. Performed in the 136-seat St. Germain Stage, it offers a personal theater experience.

FilmColumbia 2025

October 17-26, Crandell Theatre & other venues, Chatham, NY

Marking its 25th year, the FilmColumbia festival once again turns the village of Chatham into a cinephile’s haven for 10 days. This renowned small-town festival has a knack for debuting movies that go on to awards glory—past attendees saw films like Moonlight and Parasite here before they hit it big. Screenings at the newly renovated and restored Crandell Theatre and other venues feature top-notch independent, international, and documentary films, often fresh from Sundance or Cannes. Festival curators Peter Biskind and Laurence Kardish hand-pick a lineup they tout as “the very best upcoming American and international films.” Beyond screenings, FilmColumbia offers Q&As with filmmakers, panel discussions, a screenwriting workshop, and the “Saturday Night Sneak”—an unannounced mystery movie. FilmColumbia’s silver anniversary promises to be a highlight of the fall arts calendar. Just be sure to snag tickets early for buzzy evening shows, which tend to sell out.

Music & Dance

Pat Metheny – Autumn Acoustic Tour

October 4, 8pm, Mahaiwe Performing Arts Center, Great Barrington, MA

Legendary jazz guitarist Pat Metheny brings his talent to the Mahaiwe Theater for one night only. The 20-time Grammy winner will perform a solo acoustic set, switching among a dozen guitars (including his custom 42-string “Pikasso”) as he reinterprets highlights from his nearly five-decade career. Fans can expect everything from soulful ballads to impressive improvisations, interspersed with Metheny’s personal stories and insights. The historic Mahaiwe provides a cozy, resonant space to savor every note.

Alvin Ailey II Dance Company

October 17, 7:30pm, Warner Theatre, Torrington, CT

The Alvin Ailey American Dance Theater’s junior troupe (Ailey II) brings a jolt of modern dance energy to the Warner Theatre for one night. These rising-star dancers (fresh from Alvin Ailey’s rigorous training program) will perform a mixed bill blending the soulful, athletic choreography that Ailey is famous for with cutting-edge new works by emerging choreographers. The Warner’s grand auditorium will amplify the power of full-company numbers set to gospel and jazz, as well as intimate duets highlighting stunning lifts and extensions. Tickets are reasonably priced (many in the $30 to $60 range), making this a rare chance to catch world-class dance talent in Western Connecticut.

Grand Kyiv Ballet: Swan Lake

October 29, 7 PM, Warner Theatre, 68 Main St, Torrington, CT

Experience a world-class ballet company from Ukraine performing “Swan Lake” in Torrington’s Warner Theatre. The Grand Kyiv Ballet’s tour brings Tchaikovsky’s beloved ballet to life with dazzling Eastern European artistry. Expect high-level dancing, lavish sets, and costumes shipped from Kyiv. It’s a mid-week cultural experience and a chance to support international artists. Whether you’re a seasoned balletomane or a newcomer, Tchaikovsky’s timeless tale is sure to enchant. Tickets are available via the Warner box office but the venue says interest is high for this rare appearance, so don’t delay.

Davóne Tines & Ruckus – “What is Your Hand in This?”

October 25, 7 PM, Hudson Hall, 327 Warren St, Hudson, NY

Opera meets early music in this genre-blending concert at Hudson Hall. Acclaimed bass-baritone Davóne Tines, a rising star of the classical world, joins the Baroque ensemble Ruckus for a program that connects America’s musical roots with its present. Tines’s rich voice will flow from 18th-century hymns and spirituals to contemporary pieces and protest songs, all backed by period instruments like harpsichord and viola da gamba in innovative arrangements. Critics have described Tines’s performances as transformative. If you’re curious about how American history and music intertwine, this concert will be a highlight of the fall season.

Haunted Halloween Fun

Ghost Tours at The Mount

October evenings, Lenox, MA

Gilded Age glamour takes a ghostly turn at the Mount, Edith Wharton’s grand mansion in Lenox. On select nights in October, guides at Wharton’s 1902 estate lead some of New England’s spookiest ghost tours through dimly lit halls and gardens. You’ll hear about paranormal events reported when The Mount served as a dormitory—phantom footsteps on empty floors and a woman in Victorian dress believed to be Edith herself wandering the corridors. Armed only with a flashlight, visitors creep up to the third floor and even peek toward the pet cemetery where eerie figures have been seen from afar. For younger or more timid souls, there’s a tamer early-evening kids’ tour on Fridays with spooky-but-fun stories and a shorter route. All tours require advance tickets and often sell out. If you’re fascinated by literary history and the paranormal, the Mount after dark provides an unforgettable event.

Haunted Hancock Shaker Village

Thurs–Sat evenings in October, Pittsfield, MA

When darkness falls, the historic Hancock Shaker Village becomes the eerie setting for a 90-minute guided ghost tour. “Haunted Hancock” leads brave visitors by lantern light into buildings normally off-limits, sharing ghost stories and unexplained occurrences reported over the years. You’ll descend into the Brick Dwelling’s cellar to see old gravestones stored below, creep through the laundry and attic where the infamous “Woman in Black” has allegedly been sighted on the upper floors, and wander the moonlit farm grounds listening for otherworldly whispers. It’s part historical immersion, part spooky fun. Group sizes are kept small and are intended for those 12 and up (it can get quite creepy!). Tours start around 7pm; dress warmly and expect to walk outdoors between buildings.

Haunted Mill & Monster’s Ball

October 24-26, Wassaic Project, 37 Furnace Bank Rd, Wassaic, NY

For a Halloween experience that fuses art and fright, head to the hamlet of Wassaic. Each year the Wassaic Project transforms its enormous seven-story grain mill into a wildly creative haunted house art installation. Local artists and artists-in-residence take over every floor, filling dark corners with eerie sculptures, ghostly soundscapes, and interactive creepy scenes. One moment you might wander into a room of moving, haunted mechanical figures; the next, stumble upon a live performance that raises every hair on your neck. The Haunted Mill is all-ages (though it can be intense and parental discretion advised). Go early in the weekend or during the day for shorter lines. When the mill’s frights close on Saturday, the fun is just beginning: at 7pm the nearby Lantern Inn hosts the Monster’s Ball, an adults-only costume dance party with live music, over-the-top costumes, and lots of autumn revelry. Costumes are absolutely required and Monster’s Ball tickets sell out every year, so snag yours early if you plan to dance late into the night.

Hudson Halloween Parade & Trick-or-Treat

October 26, 2-6 PM, Warren St, Hudson, NY

Downtown Hudson goes all-out for Halloween with a festive afternoon that invites the whole community. From 2-4pm on Sunday, businesses along Warren Street welcome costumed kids for a cheerful trick-or-treat stroll—just look for orange pumpkin signs in shop windows to collect candy. At 4pm, the crowds converge at 7th Street Park for the kick-off of the annual Halloween Parade down Warren Street. Led by a marching band (often in costume), a stream of ghosts, superheroes, princesses, and monsters of all ages marches through the heart of Hudson, delighting onlookers and momentarily halting traffic in the name of fun. The parade ends at Hudson Hall (the historic opera house), where a big costume contest invites everyone to show off their creative outfits. Judges award prizes for categories like best family or group costume, and the whole town turns out to applaud.

Kent Pumpkin Run

October 26, 12 PM, Main St, Kent, CT

For a different kind of Halloween tradition, Kent invites you to lace up your running shoes—and maybe don a costume—for the 49th Annual Kent Pumpkin Run. This five-mile road race winds through the scenic streets of Kent at the height of foliage season, drawing hundreds of runners, many in creative Halloween costumes. It’s the town’s biggest one-day community event, with locals lining the course to cheer and a festive atmosphere all afternoon. There’s even a Kids’ Fun Run and costume contest before the main race kicks off. Organized by the Kent Chamber of Commerce, the Pumpkin Run has become a beloved tradition that mixes healthy fun with Halloween flair.

Fall Farm Highlights

High Lawn Farm

Daily in October, Lee, MA

High Lawn Farm offers a delightful pumpkin patch beside the fields populated with their gorgeous golden Jersey cows, amidst sweeping views. Visitors can pick pumpkins and enjoy classic fall treats like hot mulled cider, cider doughnuts and farm made ice cream. High Lawn Farm also hosts a special “High Lawn Halloween” event on October 25 (11am-2pm), which adds kid-friendly activities like costume contests, pumpkin painting, live music, and games.

Kesicke Farm Fall Festival

Weekends in October, Red Hook, NY

Each autumn, Kesicke Farm transforms into a bustling celebration of the harvest season, drawing families from across Dutchess County and beyond. Set against rolling farmland on the edge of Red Hook village, the festival offers everything you’d hope for in a Hudson Valley fall outing. Visitors can meander through the farm’s sprawling corn maze, pile onto hayrides that cut across fields and pastures, and visit barns filled with friendly animals waiting for a hand of grain or a scratch behind the ears. Families load wagons full of pumpkins before stopping at the farm stand, where hot cider and warm cider doughnuts have become an annual ritual. Local meats, seasonal produce, and farm-fresh goods fill out the market’s offerings, making it easy to bring a piece of the harvest home.

Naumkeag Pumpkin Show

October 1-31, Wed-Sun, 5-9pm, Stockbridge, MA

The Naumkeag Pumpkin Show runs throughout October at the Naumkeag estate in Stockbridge. From October 1-31, Wednesday-Sunday, the Gilded Age gardens are transformed by more than a thousand jack-o’-lanterns, hundreds of gourds, and imaginative pumpkin displays paired with atmospheric lighting from 5 to 9. It’s not a pick-your-own patch but an immersive visual experience great for evening strolls, photography, and family outings. Due to its popularity, parking is via shuttle and advance tickets are required, as many nights sell out.

Taft Farms

Daily in October, Great Barrington, MA

Taft Farms is a well-established Berkshires farmstand and bakery that rolls out extra autumn fun. In fall, they offer pick-your-own pumpkins, a corn maze, and hayrides on weekends. The on-site farm market and bakery offer seasonal produce, cider doughnuts, pies, and hearty lunch options, making Taft Farms a convenient all-day stop for families. There isn’t a single “festival” day here but Taft Farms provides a daily dose of fall atmosphere all season long.

Mountain View Farm

October, 10am-5pm weekdays, 9am-5pm weekends, Lanesborough, MA

Mountain View Farm offers a classic pick-your-own pumpkin experience with a laid-back vibe. The farm opens its pumpkin fields to visitors on weekends (and some weekdays) through the season. You can wander the patch and cut a pumpkin off the vine, or choose from pre-picked ones at the farm stand if you prefer. Typically the patch is open 10am–5pm on weekdays and 9am–5pm on weekends in October. It’s often less crowded than the larger tourist farms, especially early in the season, which makes for a peaceful outing against the backdrop of the Berkshire hills.