New England Fall Weekend Events 2020

New England Country Lane in the Fall

Kim Knox Beckius

During the fall foliage season, New England is a popular destination for weekenders and day trippers. If you're trying to decide when to plan your trip, or if you're looking for a reason to visit in addition to all the pretty leaves, here is a weekend-by-weekend round-up for 2020 of festivals, fairs, harvest celebrations, and other fun events in Maine, Vermont, New Hampshire, Massachusetts, Connecticut, and Rhode Island (New England) as well as in neighboring New York state.

September 7 to 8, 2020

  • Brimfield Antique Show: Head to Brimfield, Massachusetts, for the largest outdoor antique show in the country. With thousands of dealers selling everything from fine antiques to kitschy collectibles, there is plenty to see and buy. Just be prepared to walk because the grounds are vast, and you will need more than one day to visit all of the fields.  
  • Mt. Washington Valley Mud Bowl: Since 1975, North Conway, New Hampshire, has been hosting the Championship of Mud Football, called the Mud Bowl. Teams throughout New England compete in this three-day touch football tournament played in a field filled with mud. All proceeds benefit local charities.
  • Oyster Festival: If you are a fan of this saltwater bivalve or looking for a fun fall activity for the whole family, head to Norwalk, Connecticut, for the annual Oyster Festival. In addition to plenty of deliciousness on the half shell, carnival rides, arts and crafts, harbor cruises, and headline entertainment are highlights of the event.
  • 30th Annual Hampton Beach Seafood Festival: With chef demonstrations, a lobster roll eating contest, live music, a fireworks display, and seafood from 60 of the Seacoast's top restaurants, there's no better time to visit Hampton Beach, NH.

September 14 to 15, 2020

  • Maine Open Lighthouse Day: Lighthouses throughout Maine are open to the public for one day: September 8. It's a rare opportunity to step inside these heroic beacons including some that aren't routinely open to visitors.
  • The Big E: New England's largest fair, which is held in Springfield, Massachusetts, runs for 17 days, and this is the first weekend guests can indulge in all of the Big E's famously enormous food. Of course, there are amusement rides and farm animals to see, plus parades, concerts, shows, and quirky traditions like watching butter sculptors at work.
  • Boston Local Food Festival: Touting "healthy local food for all," this festival on the Greenway in Boston, Massachusetts, is free and features food from local farmers, restaurants, food trucks, and fishing boats. There are also chef demonstrations, music performances, and activities for kids.
  • Newport International Boat Show: Whether you are in the market for a new boat or just want to visit picturesque Newport, Rhode Island, this boat show is the perfect excuse to enjoy the city's stunning waterfront.
  • Telluride by the Sea: The Telluride, Colorado, Film Festival heads east for Telluride by the Sea in Portsmouth, New Hampshire each fall. View six new movies—fresh from their debut—at The Historic Theater in this seaside New England city.

September 21 to 22, 2020

  • New Hampshire Highland Games: This Lincoln, New Hampshire, weekend event showcases Scottish culture and features exciting competitions—including heavy athletics like the caber toss—plus plenty of Scottish goods and food for sale.
  • Harvestfest and "Chowdah" Cook-off: Set in the scenic mountain town of Bethel, Maine, this festival celebrates fall with a chowder cook-off, apple pie contest, music, arts and crafts, and a farmers' market.  
  • What the Fluff? Festival: Did you know that Fluff was invented in Somerville, Massachusetts? This madcap festival celebrates the marshmallow spread with live bands, silly games, and crazy contests—as well as imaginative Fluff treats to try.
  • Old Deerfield Fall Craft Fair: On the grounds surrounding Old Deerfield's Memorial Hall Museum in Deerfield, Massachusetts, is a fall arts and crafts festival that is sure to delight and impress. Shop for furniture, jewelry, apparel, pottery, and much more while enjoying live music and specialty foods.
  • Vermont Wine and Harvest Festival: Enjoy a weekend of wine tastings in and around bucolic West Dover, Vermont, featuring local vineyards, as well as artisans and gourmet food producers. The highlight of the weekend is the Grand Tasting at Mount Snow Resort: a day of wine, shopping, and scenic chairlift rides.

September 28 to 29, 2020

  • Vermont Pumpkin Chuckin' Festival: Ever wonder what happens to a pumpkin that is hurled through the air by a trebuchet? At this annual festival in Stowe, Vermont, teams compete to project pumpkins the farthest. A chili cook-off rounds out this wild event.
  • 10th Annual Great New England BBQFest at Wachusett Mountain: Bring your appetite to this two-day event in Princeton, Massachusetts, featuring not only BBQ but lively music, craft vendors, cooking demos, a farmers' market, and leaf peeping SkyRides.
  • Harpoon Octoberfest: This South Boston Octoberfest won't disappoint, with plenty of fresh Harpoon beer, oompah music, and German food.
  • Haunted Graveyard at Lake Compounce: Intended for adults and older children, this amusement park turned Halloween attraction in Bristol, Connecticut, is scary. Starting this weekend, it opens at dusk Friday through Sunday every weekend through October.

October 5 to 6, 2020

  • Jack-O-Lantern Spectacular: Walk paths through the Roger Williams Park Zoo in Providence, Rhode Island, and see hundreds of jack-o-lanterns carved into mesmerizing works of art. This nightly event runs through November 3, 2020.
  • Topsfield Fair: This agricultural fair in Topsfield, Massachusetts, celebrated its 200th anniversary in 2018. This year—over the course of 11 days—you can see racing pics, Canadian Mounties, monster trucks, New England's biggest pumpkins, and country music stars like Martina McBride.
  • Cranberry Harvest Celebration: Wade into a cranberry bog at this old-fashioned, family-fun festival in Wareham, Massachusetts, which features a juried craft show, chef demos, and helicopter rides for aerial views of the crimson-colored landscape.
  • 35th Annual Return of the Pumpkin People: Vote for your favorite pumpkin people display on a self-guided tour in and around Jackson, New Hampshire. This creative and amusing event runs the whole month of October.
  • Fall Foliage Parade: With a different theme each year, this annual parade in North Adams, Massachusetts, delights spectators with plenty of seasonal fun on the first Sunday in October.

October 12 to 14, 2020 (Columbus Day Weekend)

  • Damariscotta Pumpkinfest and Regatta: You've never experienced pumpkin mania like this! In Damariscotta, Maine, enormous pumpkins are paraded each Columbus Day weekend, and they're also dropped on cars and transformed into boats and works of art. Smaller pumpkins, on the other hand, are catapulted, raced, and turned into desserts. It's a pumpkin-flavored feast for the senses.
  • 72nd Annual Warner Fall Foliage Festival: Celebrate fall scenery in Warner, New Hampshire, with concerts, parades, a 5-mile road race, a lobster and chicken BBQ, and carnival-like fun.
  • Vermont International Film Festival: Head to Burlington, Vermont's 11-day film festival to watch screenings of dozens of feature-length films and shorts.

October 19 to 20, 2020

  • Apple Harvest Festival: Enjoy a weekend of apple goodies, alcoholic beverages, entertainment on three stages, rides, and amusements at this popular community event in Glastonbury, Connecticut.
  • Bowen's Wharf 29th Annual Seafood Festival: If you love seafood, this historic wharf in Newport, Rhode Island, is the place to be. Live bands—from blues to surf rock—add to the laid-back vibe.
  • 35th Annual Harvestfest and Kidsfest: Horse-drawn wagon rides, music, an old-fashioned market, plus plenty of local food equal a memorable fall day by the sea in York Beach, Maine.
  • 29th Annual Pumpkin Festival: Bring your jack-o-lantern to Laconia, NH, for this two-day spectacle, which culminates with the lighting of the 34-foot tower of grinning pumpkins. The line-up of events includes a zombie walk, a car show, and a duck derby, plus there are rides, concerts, and games like pumpkin bowling to amuse all ages.
  • Harvest on the Harbor: This annual food and drink festival in Portland, Maine, offers diverse delicacies for every taste.
  • Head of the Charles Regatta: Watch rowers compete in this historic regatta that takes place on the Charles River between Boston and Cambridge, Massachusetts.

October 26 to 27, 2020 (Halloween Weekend)

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