New England Fall Weekend Events 2020

Child with pumpkins at Fall Festival
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There's perhaps nowhere better to visit in the autumn than the states of New England. Apart from the gorgeous fall foliage that the region is famous for, it's also a time filled with Halloween festivals, harvest celebrations, and many more festivities, with seasonal events happening almost daily. It's also the busiest time of the year for visitors, so be sure to book reservations and make your plans well in advance if you need a place to stay.

Whether you're visiting just one of the states or completing a full New England tour—which would be Massachusetts, New Hampshire, Connecticut, Maine, Rhode Island, and Vermont—your autumn trip to the Northeast will be jampacked with non-stop events.

In 2020, many events have been canceled, postponed, or have yet to be confirmed. Be sure to check the official event webpage or local news for the latest announcements, including cancellations or new safety guidelines.

September Events

September is when the leaves first start beginning to change colors around New England, especially in the northern states of Maine, New Hampshire, and Vermont. If you're farther south near the coast, the weather should still be warm enough for end-of-season visits to the beaches of Massachusetts or in Rhode Island, but with far fewer crowds. Regardless of the area, there's plenty to enjoy in September in New England.

Massachusetts

  • 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.  The fall show takes place in early September, but it's canceled in 2020.
  • The Big E: New England's largest fair, which is held in Springfield, Massachusetts, runs for 17 days and 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. The 2020 event is canceled, but The Big E returns September 17 to October 3, 2021.
  • 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. The 2020 festival is canceled.
  • What the Fluff? Festival: Did you know that Marshmallow 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. The 2020 festival will be held virtually on September 11 with online games, trivia, and delicious Fluff recipes to try at home.
  • 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. The 2020 event is canceled, but the Craft Fair returns September 18–19, 2021.
  • 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 to get a bird's eye view of the fall foliage.
  • Harpoon Octoberfest: This South Boston Octoberfest hosted by the local Harpoon brewery never disappoints, with plenty of refreshing Harpoon beer, oompah music, and freshly-baked pretzels.

New Hampshire

  • 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, with proceeds benefiting local charities. The 2020 Mud Bowl is canceled.
  • Hampton Beach Seafood Festival: With chef demonstrations, a lobster roll eating contest, live music, a fireworks display, and seafood from 60 of the Seacoast region's top restaurants, there's no better time to visit Hampton Beach, New Hampshire. The 2020 festival is canceled.
  • Telluride by the Sea: The Telluride Film Festival takes place each September in Telluride, Colorado, but a selection of films that premiere at this world-famous festival is brought to The Music Hall in Portsmouth, New Hampshire, for Telluride by the Sea. Both the Colorado festival and Telluride by the Sea are canceled in 2020.
  • New Hampshire Highland Games: This weekend event in Lincoln, New Hampshire, showcases Scottish culture and features exciting competitions—including heavy athletics like the caber toss—plus plenty of Scottish goods and food for sale. In 2020, cultural events and performances will all take place virtually during the weekend of September 19–20.

Connecticut

  • 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. In 2020, the Oyster Festival is canceled.
  • Haunted Graveyard at Lake Compounce: Intended for adults and older children who enjoy frightening thrills, this amusement park turns into a giant Halloween attraction in Bristol, Connecticut. It normally opens in late September and runs on weekends through October, but the Haunted Graveyard won't open in 2020.

Maine

  • Maine Open Lighthouse Day: Lighthouses throughout Maine are open to the public for one special day. It's a rare opportunity to step inside these heroic beacons along the most eastern part of the U.S., including some that aren't routinely open to visitors. Open Lighthouse Day is canceled in 2020 but you can take part on September 11, 2021.
  • 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.  The festival and cook-off are canceled in 2020.

Rhode Island

  • 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. The 2020 Boat Show is canceled but it returns September 16–19, 2021.

Vermont

  • 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.
  • 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. The 2020 event is canceled, but you can chuck a pumpkin on September 26, 2021.

October Events

By October, autumn colors are in full swing across the region. This is also the peak of tourist season in New England, as visitors come from around the world to experience the fall foliage. Temperatures begin to drop and by the latter half of the month, you'll definitely need to pack some heavier layers.

Massachusetts

  • Topsfield Fair: This agricultural fair in Topsfield, Massachusetts, is one of the country's oldest and celebrated its 200th anniversary in 2018. 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. The Topsfield Fair is canceled in 2020.
  • 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.
  • 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. The 2020 parade is canceled.
  • Head of the Charles Regatta: Watch rowers compete in this historic regatta that takes place on the Charles River between Boston and Cambridge, Massachusetts. The 2020 Regatta won't take place as a weekend event, but instead is a global event that racers can participate in from any body of water.

New Hampshire

  • 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, and you can see over 80 decorated homes in October 2020.
  • 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. An alternate festival will take place virtually on October 10, 2020.
  • NH Pumpkin Festival: Bring your jack-o-lantern to Laconia, New Hampshire, 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. The 2020 Pumpkin Festival is canceled but returns October 15–16, 2021.
  • Ghosts on the Banke at Strawbery Banke: Kids can trick-or-treat at historic homes in the oldest neighborhood of Portsmouth, New Hampshire. The 2020 event is canceled.

Connecticut

  • 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.
  • Spooktacular Chili Challenge: Ready your appetite for some fiery chili at this cook-off in Simsbury, Connecticut. Live music and a costume contest add to the ambiance. The 2020 event has been modified to a drive-through event that takes place on October 18, so check the event webpage as the event gets closer for further details.

Maine

  • 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. Pumpkinfest 2020 is canceled and returns October 9–11, 2021.
  • York Harvestfest: Horse-drawn wagon rides, music, an old-fashioned market, and plenty of local food add up to a memorable fall day by the sea in York, Maine, at this annual festival. The 2020 Harvestfest is canceled but will be back on October 16, 2021.
  • Harvest on the Harbor: This annual food and drink festival in Portland, Maine, offers diverse delicacies for every taste in a city that's celebrated year-round for its culinary scene and has been called the "Foodiest Small Town in America." The 2020 festival is planned to happen but with a modified format, so check the event webpage for the most current information.

Rhode Island

  • Jack-O-Lantern Spectacular: Drive through the Roger Williams Park Zoo in Providence, Rhode Island, and see hundreds of jack-o-lanterns carved into mesmerizing works of art without having to get out of your car. This nightly event runs nightly from October 1 to November 1, 2020, and tickets must be purchased in advance online.
  • Bowen's Wharf 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. The 2020 Seafood Festival is canceled.

Vermont

  • Vermont International Film Festival: Head to Burlington, Vermont's 11-day film festival to watch screenings of dozens of feature-length films and shorts. The 2020 festival takes place from October 23 to November 1 and can be enjoyed from home, with spectators able to purchase "tickets" to screenings and then receive a link to watch the film in their own living room.
  • Essex Fall Craft and Fine Art Show: Start your holiday gift shopping early at this enduring show in Essex Junction, Vermont. Admission also includes entry to the adjacent Vermont Antique Expo and Sale. The 2020 festival is scheduled to take place on October 23–25.
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