October in New England: Best Fall Events and Travel Deals

Are you ready to have the pumpkin-spiciest October ever? New England never fails to put on a show as the leaves turn (here’s the latest foliage forecast), but there’s so much more to October than autumn colors. It’s harvest season. It’s spooky season. It’s sweater weather. October is the “last hurrah” before New Englanders brace for long, cold nights.

Destinations like 400-year-old Salem, Massachusetts, and scenic byways like the Kancamagus Highway have rightly earned the crowds they magnetize each October. But New England is so multifaceted. Some of my favorite October events happen in unexpected places, from urban zoos to rural communities. And here’s what I love about planning a day, weekend, or longer getaway around one of New England’s best fall events: You won’t feel the slightest bit disappointed if the fall foliage is pre-peak or post-peak. Mother Nature’s glitter is all just a bonus.

Can’t get to New England in October? Page through our fall issue of Yankee online, and join us in spirit. But I hope this guide to the month’s best weekend happenings and travel deals will convince you to get on the road. New England celebrates autumn like nowhere else on earth, and you’ll be glad you carved out time to make memories.

Weekend of October 3–4, 2026

Topsfield Fair | Topsfield, MA

It’s opening weekend for the Topsfield Fair, which runs October 2–12 (so get there next weekend if you miss it this weekend). For the 42nd year, the All New England Giant Pumpkin Weigh-Off takes place on the fair’s opening day (Friday, October 2), and these gentle giants remain on display throughout the event’s 11-day run. This classic New England fair has delighted kids and adults for more than 200 years (we wrote a book about that), and it strikes just the right balance of agricultural exhibits, Midway entertainment, shows, parades, and over-the-top food like the Gobbler Sandwich: Thanksgiving dinner on a stuffing-flavored roll.

Freeport Fall Festival | Freeport, ME

Downtown Freeport welcomes more than 200 of New England’s top makers, artists, and specialty food producers for a three-day celebration of autumn October 2–4. The annual Freeport Fall Festival also features live music and hands-on activities for kids and families, and it’s all free. Be sure to visit the newly reopened and reimagined L.L.Bean flagship store (here’s a look inside from my visit in September).

Scot-tober Fest at The Anchor | Charlestown, MA

The Tartan Army is returning to Boston, and you’ll want to join those merry Scottish football (soccer) fans at The Anchor, especially if you missed all of the fun when this waterfront venue and beer garden became Scotland House during the World Cup. Scot-tober Fest features a pre-party on Friday, October 2; a watch party when Scotland plays North Macedonia at 2:45 p.m. on Saturday, October 3; and a Patriots watch party on Sunday, October 4, at 1 p.m.

Guilford Porchfest | Guilford, CT

Got a lawn chair? Then, you have everything you need to attend Guilford Porchfest. On Saturday, October 3, 50 porches throughout this Connecticut shoreline community will host free live performances by locals. It’s a celebration of just how much talent resides within this town known for its thriving arts scene.

Mount Snow Oktoberfest | Dover, VT

Mount Snow Oktoberfest is so popular, the mountain resort is doubling down again this year with two Saturdays of traditional, German-style fun on October 3 and October 10. Admission is free, and guests will discover winter hangouts transformed into beer halls for this 28th annual autumn ritual. In addition to traditional Oktoberfest fare, there’ll be music, games, and activities for all ages. The Mount Snow Oktoberfest Craft Fair occupies the Main Base Lodge and spills just outside, too. And this year’s Stein Holding and Keg Throwing competitions are open to all: Just be among the first to register. Próst!

The Great Pratt Street Autumn Festival | Hartford, CT

Calling all Gilmore Girls fans! On October 3 and 4, downtown Hartford’s Pratt Street is being transformed for the Great Pratt Street Autumn Festival (formerly Stars Hollow Saturday). Dress up in Lorelai style and have a cup of coffee, join in a Miss Patty-style dance class, hear a barbershop quartet, participate in a knit-a-thon, browse at the River Bend book truck, and shop for Stars Hollow-inspired merch at Hartford Prints! Admission is free with an online RSVP.

Columbus Day and Indigenous Peoples’ Day Weekend, October 10–12, 2026

Fall Fest at Sunday River | Newry, ME

Saturday’s 27th Annual North American Wife Carrying Championship is the highlight of the free, two-day Fall Fest at Sunday River, October 10–11. It’s hysterical for spectators, and the winners walk away with the wife’s weight in beer and five times her weight in cash. Crafts, food, scenic gondola rides, and music are among the other offerings.

Paradise City Arts Festival | Northampton, MA

Stunning works of visual, wearable, functional, and decorative art make fall’s annual Paradise City Arts Festival a holiday weekend must for anyone who wants to acquire finely made things for their home or for holiday gifting. The indoor-outdoor show brings 200 juried makers and artists from across the country together in one beautiful, inspiring spot, just as leaves are adding their own artistry to the landscape.

Tractor Parade | East Charlotte, VT

The annual Tractor Parade in East Charlotte, Vermont, is a slow-moving procession that’s an absolute delight to behold. On Sunday, October 11, bring a chair and join in this free community celebration of farming, which also features food, music, games, and family-friendly activities.

Hartford Stage Presents Dracula | Hartford, CT

Morgan Lloyd Malcolm’s adaptation of Bram Stoker’s classic Dracula earned acclaim in London, and this month is your chance to see this bold, contemporary take here in New England. Dracula opens at Hartford Stage on Friday, October 9, with two additional performances this weekend and additional dates through November 1. While you’re in Hartford, be sure to dine at the newly reinvented Carbone’s. The city’s Italian standout reopened in a new location last month after a six-year closure.

Weekend of October 17–18, 2026

Head of the Charles Regatta | Boston and Cambridge, MA

The world’s largest rowing competition, the Head of the Charles Regatta, has been a fall tradition for more than six decades. This three-day thrill for spectators coincides with one of the best urban leaf-peeping weekends in New England, October 16–18. In addition to watching teams and individuals from around the globe competing on the Charles River, you’ll be able to sample Boston eats and try out equipment at the Rowing and Fitness Expo at the finish line.

Harvest on the Harbor | Portland, ME

Maine’s foodie city is the place to be this weekend, as Harvest on the Harbor adds additional allure to Portland’s famed culinary scene. The event kicks off Friday afternoon, October 16, with the Maine Lobster Chef of the Year competition. Additional ticketed events on Saturday, October 17, celebrate Maine oysters.

Jack-O’-Lantern Spectacular at McLaughlin Garden and Homestead | South Paris, ME

From Thursday through Saturday, October 15–17, the peaceful grounds of this 1840s farmstead are transformed for a Jack-O’-Lantern Spectacular that is delightfully imaginative. This year’s enchanted forest theme will be brought to life in displays incorporating more than 500 locally grown pumpkins, carved by volunteers, and visitors are encouraged to dress as their favorite magical characters. Admission to this display of fairies, gnomes, and more includes warm spiced apple juice.

New Hampshire Film Festival | Portsmouth, NH

The Music Hall has assembled quite a lineup for the 24th annual New Hampshire Film Festival, which runs October 15–18 at a variety of venues in New Hampshire’s seaside city. More than 100 films by creators from around the world will be screened during the four-day festival. A discounted pass for film buffs 40 and under is back again this year.

Ghosts on the Banke at Strawbery Banke | Portsmouth, NH

The preserved historic neighborhood of Strawbery Banke welcomes back some long-gone residents for Ghosts on the Banke: a spooky yet family-friendly exploration of ghostly lore, plus much more. Held during two weekends in 2026, October 16–17 and October 23–24, kids can trick-or-treat at historic houses, create giant spider webs, and meet pirates, and you’ll all love dancing, seeing carved pumpkins aglow, and—new for 2026—meeting long-gone locals via haunting projections.

Weekend of October 24–25, 2026

Halloween Ball | Salem, MA

On Saturday, October 24, celebrate Halloween at the Hawthorne Hotel’s popular Halloween Ball. This year’s costume theme is Phobia, and facing your fears is the focus of this unforgettable 21+ evening featuring a live band, two DJs, food stations, a cash bar, and interactive experiences. Be sure to reserve tickets in advance.

Witches of Wickford Paddle | Wickford, RI

You’ll be hard pressed to find a more photogenic event in New England this weekend! On Sunday, October 25, gather early to watch The Kayak Centre of Rhode Island’s annual Witches of Wickford Paddle featuring colorfully costumed participants who’ve traded brooms for paddles. They’ll be on the water from noon until about 2 p.m. Rain date is Saturday, October 31.

Home Team Weekend at L.L.Bean | Freeport, ME

24-hour shopping is back at L.L. Bean’s flagship store after a two-year renovation, and after five weekends of celebrating the Grand Opening, Home Team Weekend is set to rock visitors with a free outdoor concert by The Wallflowers on Friday evening, October 23, and appearances all weekend long by players from the Boston Red Sox and the Portland Hearts of Pine. And there’ll be more sporty surprises, too (I have a hunch the Hearts’ moose mascot, Moxie, will be on the scene!).

Gilfeather Turnip Festival | Wardsboro, VT

Turnips take center stage every year at this celebration featuring everything from tastings to all-day-long screenings of The Turnip Movie. The Gilfeather Turnip Festival has been a tradition since 2001, and there’s no harvest happening quite like it. Head to Wardsboro on Saturday, October 24, and you can sip turnip soup while you browse the market and the book sale, listen to music, marvel at the turnip contest winners, and shop for turnip seeds to plant next season.

Hot Air Balloon Glow Night | Morris, CT

South Farms hosts a spectacle from 5–8 p.m. on Saturday, October 24, when Hot Air Balloon Glow Night transforms the property into a magical autumn destination. Tickets are $40 per carload of up to four guests and should be purchased in advance. There’ll be food and drinks for purchase and music for ambience. Rain/wind date is Sunday, October 25.

Pumpkin Carving & Fireside Storytime at ArtWaves | Bar Harbor, ME

As Halloween approaches, spend an evening at ArtWaves, and go home with carved pumpkins to decorate your doorstep. Registration for Pumpkin Carving & Fireside Storytime on Sunday, October 25, from 5 until 7:30 p.m. is required and only $15 for a family of up to four. Pumpkins will be provided, along with cider and hot cocoa, and members of ArtWaves’ in-house improv troupe will lead an interactive storytelling and games session.

Weekend of October 31–November 1, 2026

Halloween on the Hill | Farmington, CT

The Hill-Stead Museum’s rural hilltop grounds are an enchanting place to take your costumed littles on Saturday, October 31, for a memorable afternoon of hayrides, treats, and flinging pumpkins with a slingshot to feed the sheep! Halloween on the Hill also features surprises throughout the picturesque grounds. Tickets are $5 per person or $20 per carload and should be reserved in advance.

New This Month in New England

Jack-O-Lantern Spectacular at Roger Williams Park Zoo | Providence, RI

This year’s Jack-O-Lantern Spectacular at Roger Williams Park Zoo in Providence, Rhode Island, has a new twist. As you navigate the Great Pun-Kin Trail (that’s not a typo), you’ll encounter groan-worthy puns and other playful characters and scenes, all designed to bring dad-joke-level levity to your experience of the most mind-blowing display of carved pumpkins in New England. See these 5,000 professionally carved, illuminated pun-kins on display nightly, October 1 through November 1 (the final night is 21+ only). Timed tickets should be purchased online in advance.

Concord’s Black Heritage Trail | Concord, MA

On October 22 at noon, you’re invited to attend the dedication of Concord’s new Black Heritage Trail at Freedom Park in Monument Square. It’s an important moment for the town, which has installed 10 trail markers and created a Black Heritage Walking Tour to surface untold stories and commemorate the lives of individuals who played important roles in the town’s and America’s history.

Maine State Museum | Augusta, ME

One of the nation’s oldest state-funded museums has been undergoing a facelift, and you can see phase one revealed at a Grand Reopening on Saturday, October 24. What will you see? How about the only pair of female and calf humpback whale skeletons on display anywhere, for starters.

October’s Best Travel Packages, Deals, and Special Offers

Falling For You Savings at Colonial Inn | Ogunquit, ME

Cuddle up on the Maine coast this fall, and save 15 percent with code FALL4U when you stay two midweek nights through October 30 at Colonial Inn. The Falling For You getaway deal also includes a guide to fall in Ogunquit. Rates start at $134 per night, double occupancy, with the discount.

Win a Trip to Ireland | Portland, ME

Rí Rá Irish Pub in Portland, Maine, is celebrating its 25th anniversary during the last week of October, and they expect to pour their one-millionth pint of Guinness! Be there October 28–30 for Anniversary Celebrations including live music and a meet and greet with the founders, and if you’re the lucky person to order Guinness number one million, you’ll win a trip for two to Ireland.

Yankee Out & About in October and Beyond

Longtime Yankee editor Mel Allen continues his book tour this month with stops in Massachusetts, New Hampshire, and Pennsylvania. Can’t make it to an event? Mel’s book, Here in New England, can be ordered from our online Yankee Shop.

Celebrate the holidays with us! Tickets are on sale now for Yankee Magazine’s New England Holiday Table Dinner on December 12 at 6 p.m., in collaboration with LaBelle Winery in Amherst, New Hampshire. Space is limited, especially for the VIP experience, so treat yourself to tickets while they last.

This post is edited annually; last updated for October 2026.

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