30 Things To Do in October

Posted On : October 05, 2026

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October is showing off with peak foliage, pumpkins, apple cider and a packed calendar of things to do. From New Haven to Mystic, we found fall festivals, art shows, live music, theater, foodie happenings, foliage cruises and plenty of Halloween fun. Here’s where to make the most of one of the best months of the year.

10/7 | 4th Annual Health & Wellness Expo | Branford
Spend the morning discovering local resources for feeling your best, with health and wellness experts, services and plenty of useful information gathered under one roof. $50

Select Nights 10/9–10/30 | What Lurks Beneath: Ghost Ship at Mystic Seaport Museum | Mystic
Ghostly whalers take over the waterfront in this immersive Halloween adventure filled with live music, wild storytelling, swashbuckling and spooky encounters. Explore at your own pace, if you dare. $27 – $46

10/10–10/11 | Hadlyme Hall’s Artists & Friends Art Show | Hadlyme
A beloved fall tradition returns with original work from local artists filling historic Hadlyme Public Hall. Browse paintings, ceramics, photography, jewelry, woodwork and more over one beautiful autumn weekend.

10/10 | October Open Trails + Music at I-Park | East Haddam
Wander 40+ artworks tucked throughout I-Park’s meadows and woodlands, join a guided hike, make some art, then spread out a picnic for live music by The Midnight Anthem. Free, donations welcome.

10/10 | Fall Artisan Market & Guilford Flavors & Finds | Guilford
Shop local makers on the Green, then taste your way through downtown with food and drink samples, special offers and fun stops at Guilford shops and restaurants. Free.

10/17–10/18 | Mystic Apple Festival at Olde Mistick Village | Mystic
Celebrate everything fall with artisan vendors and seasonal treats featuring all the good stuff like apples, pumpkin, maple and caramel all throughout Olde Mistick Village. Free.

Thru 10/18 | The Snow Goose at Goodspeed Musicals | East Haddam
A wounded snow goose brings two unlikely friends together on England’s windswept coast as World War II approaches. A moving new musical about friendship, courage and letting go. $35-$125.

Thru 10/31 | Fall Festival at Bishop’s Orchards | Guilford
Apple picking, wagon rides, pumpkins, a four-acre corn maze, cider and food trucks, basically everything required for a proper New England fall afternoon. Prices vary.

Thru 10/31 | Sightseeing & Fall Foliage Cruises from Connecticut River Museum | Essex
See the lower Connecticut River dressed for fall from the best seat around, the water. Choose RiverQuest or historic Onrust for foliage, wildlife and spectacular river views. Prices vary.

10/31 | Trunk or Treat | Madison
Costumes, candy and creatively decked-out cars take over the Madison Town Green for this family-friendly Halloween tradition. Bring your trick-or-treat bag and make the rounds.

Thru October | Corn Maze, Wagon Rides & Pick Your Own at Scott’s Yankee Farmer | East Lyme
Pick apples straight from the trees, hunt down the perfect pumpkin and reward yourself with an apple cinnamon donut. Fall doesn’t get much more New England than this. Prices vary.

Thru 11/1 | Wee Faerie Village: Gemstone Station: A Town That Rocks at Florence Griswold Museum | Old Lyme
The Wee Faeries are back and this year they sparkle. Tiny dwellings inspired by gemstones, minerals and shimmering metals transform the Museum grounds into one wonderfully imaginative little world. $21 – $23.

Thru December | “Not So Obvious” Game Night at Yankee Cider Company | East Haddam
Part trivia, part Connections and apparently not as obvious as you think. Gather a team, order a cider and see who can uncover the hidden links first.

Thru 1/3 | Isaac Sheffield: Portraits from New London’s Whaling Era at Lyman Allyn Art Museum | New London
Meet the faces of 19th-century New London through portraits by local artist Isaac Sheffield, painted when whaling fortunes were booming and the city was finding its place in the world. Free with General Admission.

Thru 7/25/27 | John Constable: The Landscape Reimagined at Yale Center for British Art | New Haven
Clouds, changing light and windswept landscapes take center stage in the only major U.S. exhibition marking the 250th anniversary of one of Britain’s most influential painters. Free.

Ongoing | Connecticut Oyster Trail | Statewide
Slurp your way around Connecticut with stops at oyster farms, raw bars and restaurants celebrating our homegrown bivalves. A very tasty excuse for a shoreline road trip.

10/1–10/25 | A Piece of My Heart at Ivoryton Playhouse | Ivoryton
Six women who served in Vietnam share stories too often left untold in this powerful play with music about courage, sacrifice, friendship and the lasting cost of war. $25-$65

10/8 & 10/15 | Art•Bar: Bespoke Faerie Dwellings at Florence Griswold Museum | Old Lyme
An adults-only excuse to play with the faeries. Sip something delicious while creating your own tiny dwelling inspired by Gemstone Station during FloGris’s popular evening art series. $40 (Members 10% discount).

10/10–10/11 | Season 36 Opening Concerts with Musical Masterworks | Old Lyme
What makes music sound American? Tessa Lark, Edward Arron, Jeewon Park and Melissa Reardon explore the question through Montgomery, Copland, Clarke, Perkinson and Dvořák. Saturday 5pm; Sunday 3pm. $45

10/18 | Yellow Farmhouse Culinary Carnival at Stone Acres Farm | Stonington
Future farmers and curious foodies can get their hands dirty with veggie sushi, miso, natural dyes, oysters and more, plus live music, food and plenty of farm fun. Tickets on sale soon.

10/24 | Sip & Savor: Mocktail & Small Plates Tour at The Shops at Yale | New Haven
Five downtown restaurants, five inventive zero-proof cocktails and five chef-inspired small plates. The inaugural Sip & Savor offers a tasty new way to eat your way around New Haven. $30

10/24 | The Great Main Street Pumpkin Fest | Old Saybrook
Main Street gets a fall makeover with an afternoon of crafts and activities, sips and snacks, live music, shopping and plenty of family-friendly fun. Costumes encouraged. Free.

10/24 | Ivoryton Village Pumpkin Festival | Ivoryton
Ivoryton glows with hundreds of jack-o’-lanterns plus a costume parade, live music, hayrides, face painting, Trunk-or-Treat and plenty of Halloween mischief. Free.

10/24 | Pirate Day at Wee Faerie Village | Old Lyme
Ahoy, faeries! Pirates invade Gemstone Station for an afternoon of swashbuckling fun among the miniature dwellings. Come dressed for adventure and explore the Museum grounds. Free with admission.

10/26 | Halloween Moonlight Social at Stone Acres Farm | Stonington
Dance under the October moon with DJs, live performers, cocktails, local eats and mesmerizing hoop and ribbon dancers, then wind down by the bonfire with meditation and sound healing. $26.

10/29 | The Legend of Sleepy Hollow at Essex Library | Essex
Dim the lights. Michael Langlois brings Washington Irving’s spooky classic to life as Ichabod Crane encounters the legendary Headless Horseman. A perfectly timed dose of Halloween suspense. Free.

10/30–12/27 | Annie — 50th Anniversary at Goodspeed Musicals | East Haddam
Annie comes home. Fifty years after the musical premiered at Goodspeed, a brand-new production brings Miss Hannigan, Daddy Warbucks, Sandy and those irresistible songs back to where it began. $47 – $120.

10/31 | Rock a Costume: Halloween in Gemstone Station at Florence Griswold Museum | Old Lyme
Costumes meet crystals for the final Saturday of Wee Faerie Village. Dress up, wander among the sparkling miniature worlds and celebrate Halloween Flo Gris-style. Free with Admission.

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