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, 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 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 4-5, 2025

Topsfield Fair | Topsfield, MA

It’s opening weekend for the Topsfield Fair, which runs October 3-13 (so get there next weekend if you miss it this weekend). For the 41st year, the All New England Giant Pumpkin Weigh-Off takes place on the fair’s opening day (Friday, October 3), 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.

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 4 and October 11. Admission is free, and guests will discover winter hangouts transformed into bier halls for this 27th 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 Mount Snow has partnered with Stowe’s von Trapp Brewing to host this year’s Stein Holding Competition. Próst!

Stars Hollow Saturday | Hartford, CT

Calling all Gilmore Girls fans! For one day only, October 4, downtown Hartford’s Pratt Street is being transformed for Stars Hollow Saturday. Dress up in Lorelai style and have a cup of Luke’s Diner coffee, join in a Miss Patty’s Dance Class, play Gilmore Girls trivia, participate in a knit-a-thon, board the Pedal Pub and tour Emily Gilmore-approved historic sites, and shop for Stars Hollow-inspired merch. Promo code dragonfly will save you 10 percent on stays at Hartford’s Goodwin Hotel.

Columbus Day and Indigenous Peoples’ Day Weekend, October 11-13, 2025

Fall Fest at Sunday River | Newry, ME

Saturday’s 26th Annual North American Wife Carrying Championship is the highlight of the free, two-day Fall Fest at Sunday River, October 11-12. 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 12, bring a chair and join in this free community celebration of farming, which also features music, games, and activities in the Field of Fun.

Weekend of October 18-19, 2025

Head of the Charles Regatta | Boston and Cambridge, MA

The world’s largest rowing competition, the Head of the Charles Regatta, is celebrating 60 years in 2025. This three-day thrill for spectators coincides with one of the best urban leaf-peeping weekends in New England, October 17-19. 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.

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

From Thursday through Saturday, October 16-18, the peaceful grounds of this 1840s farmstead are transformed for a Jack-O’-Lantern Spectacular that is delightfully imaginative. This year’s prehistoric theme will be brought to life in displays incorporating more than 300 locally grown pumpkins, carved by volunteers. Admission to this display of dinosaurs and more includes warm spiced apple juice and photo booth fun in the barn.

New Hampshire Film Festival | Portsmouth, NH

The Music Hall has assembled quite a lineup for the 23rd annual New Hampshire Film Festival, which runs October 16-19 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. Expanded to two weekends in 2025, October 17-18 and October 24-25, 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 warming up by the All Hallows Bonfire.

Weekend of October 25-26, 2025

Halloween Ball | Salem, MA

On Saturday, October 25, celebrate both Halloween and the Hawthorne Hotel’s 100th anniversary at the property’s popular Halloween Ball. This year’s costume theme is A Vintage Hallowe’en, and nostalgia will infuse this unforgettable evening featuring a live band, two DJs, food stations, a cash bar, and interactive experiences. Be sure to reserve tickets in advance.

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 25, 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.

Stained Glass for Beginners at ArtWaves | Bar Harbor, ME

As the landscape begins to quiet and fade, spend a day at ArtWaves learning the art of stained glass, and go home with a sun-catching flower, hummingbird, or other creation that will bring light into your home and a smile to your face all winter long. Instructors Dave and Lisa Roy have 20 years of experience working with stained glass. You need zero experience, but pre-registration is required.

New This Month in New England

Rocky Horror Picture Show 50th Anniversary Events

Spooky season wouldn’t be complete without screenings of cult classic The Rocky Horror Picture Show. You’ll have abundant opportunities to throw toast here in New England this month. Here are some of the places where the iconic film will be celebrated on its 50th anniversary:

• Emerson Colonial Theatre, Boston, MA (October 1, with Barry Bostwick)
• Fairfield Theatre Company, Fairfield, CT (October 24)
• Chunky’s Cinema Pub, Manchester, NH (October 25)
• The Opera House, Enosburg Falls, VT (October 25)
• Warner Theater, Torrington, CT (October 30, with Barry Bostwick)
• Arts at the Armory, Somerville, MA (October 30)

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 “Trivia 2nd-Edition” theme that adds an all-new twist of fun to what is annually the most mind-blowing display of carved pumpkins in New England. Test your knowledge nightly through November 2.

October’s Best Travel Packages and Deals

Falling For You Savings at Colonial Inn | Ogunquit, ME

Cuddle up on the Maine coast this fall, and save 10 percent with code FALL4U when you stay two midweek nights through October 31 at Colonial Inn. The Falling For You getaway deal also includes apple cider mimosas and a guide to fall in Ogunquit. Rates start at $80.10 per night, double occupancy, with the discount.

Apple Harvest Package at the Fairmont Copley Plaza | Boston, MA

A copy of The Apple Lover’s Cookbook by Yankee‘s own senior food editor and Weekends with Yankee cohost Amy Traverso is among the treats you’ll enjoy when you book this special getaway, available through October 31. A flight of Massachusetts-grown apples from the Copley Square Farmers Market will be waiting for you, and you’ll also get to savor mulled cider and Spiced Apple Cupcakes with Cinnamon Cream Cheese Frosting: a Traverso recipe prepared by the hotel’s culinary team. Overnight rates for the package start at $549, excluding taxes and fees.

Yankee Out & About in October

Get your tickets now, and join us on October 16 for the Boston Public Market’s Harvest Party. This year, the market is celebrating its 10th birthday during the nonprofit’s annual fundraiser, and Yankee is pleased to be a media sponsor for the event.

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

Kim Knox Beckius

Kim Knox Beckius is Yankee's travel & branded content editor. A longtime freelance writer/photographer and Yankee contributing editor based in Connecticut, she has explored every corner of the region while writing six books on travel in the Northeast and contributing updates to New England guidebooks published by Fodor's, Frommer's, and Michelin. For more than 20 years, Kim served as New England Travel Expert for TripSavvy (formerly About.com). She is a member of the Society of American Travel Writers (SATW) and is frequently called on by the media to discuss New England travel and events. She is likely the only person who has hugged both Art Garfunkel and a baby moose.

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