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 Kancamaugus 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 5-6, 2024

Topsfield Fair | Topsfield, MA

It’s opening weekend for the Topsfield Fair, which runs October 4-14 (so get there next weekend if you miss it this weekend). For the 40th year, the New England Giant Pumpkin Weigh Off takes place on the fair’s opening day (Friday, October 4), 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, 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 this year with two Saturdays of traditional, German-style fun on October 5 and October 12. Admission is free, and guests will discover winter hangouts transformed into bier halls for this 26th 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 returns after a long hiatus. And Mount Snow has partnered with Stowe’s von Trapp Brewing to host preliminary qualifying rounds of the Vermont State Steinholding Championships. Próst!

Stars Hollow Saturday | Hartford, CT

Calling all Gilmore Girls fans! For one day only, October 5, 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, hear a barbershop quartet, bob for apples, and shop for Stars Hollow-inspired merch.

Columbus Day and Indigenous Peoples’ Day Weekend, October 12-14, 2024

Fall Fest at Sunday River | Newry, ME

Saturday’s 25th Annual North American Wife Carrying Championship is the highlight of the free, two-day Fall Festat Sunday River, October 12-13. 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. Celebrating 30 years in 2024, the indoor-outdoor show brings 220 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 13, 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 19-20, 2024

Head of the Charles Regatta | Boston and Cambridge, MA

The world’s largest rowing competition, the Head of the Charles Regatta, is a three-day thrill for spectators that coincides with one of the best urban leaf-peeping weekends in New England, October 18-20. 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.

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

From Thursday through Saturday, October 17-19, the peaceful grounds of this 1840s farmstead are transformed for a Jack-O’-Lantern Spectacular that is delightfully imaginative. This year’s circus theme will be brought to life in displays incorporating more than 300 locally grown pumpkins, carved by volunteers. Admission includes hot cocoa or warm apple cider, popcorn, and photo booth fun in the barn.

New Hampshire Film Festival | Portsmouth, NH

The Music Hall has taken the reins this year and assembled quite a lineup for the 22nd annual New Hampshire Film Festival, which runs October 17-20 at a variety of creative 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 new this year.

Weekend of October 26-27, 2024

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 actually kicks off Thursday evening, October 24, with the Maine Cocktail Classic, a sampling event for spirits lovers. Additional ticketed events on Friday and Saturday, October 25-26, celebrate the best of Maine’s ocean bounty. Who will be crowned Maine Lobster Chef of the Year? Be there Friday to toast the winner.

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. From October 24-27, 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.

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 “Trivia 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.

Titanic: The Artifact Exhibition | Boston, MA

The fascination with Titanic goes on and on, and you can see recovered relics from the ill-fated ship when Titanic: The Artifact Exhibition makes its New England debut this month. This interactive installation, which runs through February 2 at the Saunders Castle at Park Plaza in Boston, features a full-scale recreation of the Grand Staircase and other ship interiors. You’ll receive a replica boarding pass, assume the ID of a passenger, and experience the Titanic story in deeply moving ways.

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% 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 10% 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 co-host 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 Executive Chef Zaid Khan and the hotel’s culinary team. Overnight rates for the package start at $559, excluding taxes and fees.

Yankee Out & About in October

Join us in celebrating the October 1 release on Apple TV of Another Happy Day. Yankee‘s Senior Features Editor Ian Aldrich is proud to have worked on this feature film (watch the trailer). If you’re more a fan of independent cinema than streaming services, you can also see the movie screened at the Peterborough Community Theatre in Peterborough, New Hampshire, from September 27 through October 3.

Love interior decorating and all things home and design? Get tickets now for DESIGN identities: FALL MARKET AT the Boston Design Center on Tuesday and Wednesday, October 8 and 9, and you’ll be enchanted by the lineup of book signings, product launches, and panel presentations. Kate Weeks, Yankee‘s director of marketing and business development, will moderate the “Home Sweet Home? Designing For Tomorrow’s Living & Working” conversation on Tuesday morning.

Get your tickets now, and join us on October 17 for the Boston Public Market’s Harvest Party. This year, the market is being transformed into a carnival for the non-profit’s annual fundraiser, and Yankee is pleased to be a media sponsor for the event.