September in New England: Best Events and Travel Deals

September is a month of transition in New England. Even after Labor Day signals playtime is over, some September days feel summerlike. And then, one evening or early morning, you feel it: that cool, crisp zing in the air that heralds fall’s arrival.

If you are kid-less or have preschoolers, September is an ideal month for an extended vacation in New England—perhaps even a honeymoon. The first two or three weeks of the month are a best-kept secret: Lodging rates tend to be low during this brief window. That’s because many families with school-age children aren’t able to travel, and fall foliage season is not yet in full swing (but once it gets underway, our official foliage forecast says we’re in for a brilliant, extended color show this year). Travel in early September, and you’ll avoid crowds, you may spy some early hints of autumn color, and you can still go for a swim in sun-warmed lake or ocean waters.

Best of all, the region’s calendar is loaded with fun events this month: agricultural fairs, festivals, sporting events. Shorter daylight hours and bursts of cool weather are a reminder to savor September’s splendor. I’ll help you do just that with my event picks for all four September weekends, plus the inside scoop on some of early fall’s best deals and a few new things to do in New England.

Yankee Out & About This Fall

A Revolutionary Feast: Dinner with Amy Traverso | Canton, MA

Join your host, Yankee senior food editor Amy Traverso, for a celebration of the 250th anniversary of America’s independence. Tickets are on sale now for A Revolutionary Feast on Wednesday, September 16, at Northern Spy, kicking off with a cocktail reception and passed appetizers at 5:45 p.m. Northern Spy chef/co-owner Marc Sheehan has engineered an unforgettable three-course menu, inspired by New England’s culinary history but reimagined through a modern lens. Chef Marc’s expertise as a food historian means that you’re in for some colorful storytelling as you break bread with new friends. Sponsored by Yankee, the dinner extends upon the “Harvest Time” episode from the current season of Weekends with Yankee, in which Amy explores Indigenous and early American food traditions alongside Sheehan and Wampanoag culinary expert Malissa Costa of Plimoth Patuxet Museums.

Meet Mel Allen

Yankee‘s longtime editor, now editor at large, Mel Allen is the author of the popular book Here in New England, featuring four decades of his best writing, and you can catch Mel at one of the many book-tour events he has scheduled this fall. I’m planning to be there to support Mel on September 21 at 6 p.m. at the library in Southwick, Massachusetts, so please say hi if you’re able to attend.

Register for Yankee’s Fall Foliage Webinar

Join us on Monday, September 14, at 7 p.m. EDT for a live online webinar, where Yankee foliage expert Jim Salge will discuss his 2026 forecast, plus the chemistry behind the color change and the impact of weather patterns on the intensity of the season. Whether you are a lifelong New Englander or a first-time leaf peeper, this session will change the way you look at the woods this fall. Register free now!

Weekend of September 5-7, 2026 | Labor Day Holiday Weekend

Garlic Town, USA! | Bennington, VT

Start your Labor Day weekend in New England at a destination that comes to life just one day each year: Garlic Town, USA! On Saturday, September 5, more than 130 purveyors of garlicky goods will gather in downtown Bennington, Vermont, to tantalize your tastebuds (yes, there will be garlic ice cream). This beloved community festival is about more than the venerable bulb, though. Bands play all day, chefs and farmers offer talks and demonstrations, there are games and activities for kids and adults, and the bar tent serves up Garlic Bloody Marys. Save on admission by purchasing tickets online in advance.

King Richard’s Faire | Carver, MA

New England’s largest and longest-running Renaissance festival kicks off its 45th season this weekend, and you’ll have a realm of opportunities to visit King Richard’s Faire on weekends and Monday holidays through October 25. Do go in costume … and do devour a giant turkey leg.

Gilmore Girls Fan Festival | New Milford, CT

A Weekend in the Life is a three‑day celebration of all things Gilmore, set in a Connecticut town many fans believe is the closest thing to Stars Hollow. From Friday, September 4, through Sunday, September 6, meet cast members including Scott Patterson (Luke!) and Sean Gunn (Kirk!), compete in trivia and other contests, make crafts, attend parties, and mingle with others who would give anything to be besties with Lorelai and Rory. VIP weekend packages and single-day tickets can be purchased online.

Rubber Ducky Regatta | North Woodstock, NH

Spend Labor Day Monday, September 7, in the White Mountains cheering on 1,500 bright yellow rubber ducks. It’s the 30th year for this beloved tradition, and the Rubber Ducky Regatta in Cascade Park is more than a spectacle. When you adopt a duck (or a flock), you’ll have the chance to win fabulous prizes, and you’ll also be supporting the Western White Mountains Chamber of Commerce scholarship fund. And all of the family-friendly entertainment in the build-up to the big race is free to enjoy.

Weekend of September 12-13, 2026

Maine Open Lighthouse Day | Various Locations

On Maine Open Lighthouse Day, Saturday, September 12, lighthouse lovers can experience more than a dozen of Maine’s cherished beacons in unique ways. Climb lighthouse towers (even Portland Head Light if you’re among the first 280 visitors), tour keepers’ quarters, and view special exhibits. At Owls Head Lighthouse, meet Angeli Perrow, author of the children’s book Lighthouse Dog to the Rescue.

Weekend of September 19-20, 2026

New England Fall Flower Show | Wellesley, MA

The Massachusetts Horticultural Society has reimagined its annual flower show as an autumn event, and Yankee is proud to be a media partner for this year’s New England Fall Flower Show at the Garden at Elm Bank. Expanded to four days, the festivities kick off with a Thursday night preview party on September 17 and continue Friday through Sunday with displays, vendors, and speakers including my colleague Carol Connare, 14th editor of The Old Farmer’s Almanac. Carol’s talk, Old Farmer’s Almanac, Guiding Gardeners for 235 Years and Counting, is scheduled for Friday, September 18, at 2:30 p.m. Purchase timed-entry tickets online in advance.

The Big E | Springfield, MA

It’s opening weekend for New England’s mega-fair, The Big E, which promises nonstop fun from September 18–October 4. Yes, there are agricultural competitions, concerts, and carnival rides, plus a daily Mardi Gras Parade. And everyone loves noshing and shopping their way through the replica statehouses from all six New England states. But the most tantalizing attraction at the fourth largest fair in North America is over-the-top food, from deep-fried Kool Aid to giant cream puffs. New this year: The Big E celebrates America’s 250th birthday with red, white, and blue theming; concerts by performers like The Beach Boys and Brad Paisley; and patriotic attractions, including a Wreaths Across America display to honor veterans during the first six days of the fair.

NH Highland Games & Festival | Lincoln, NH

From September 18-20, all things Scottish are a short drive away if you live in New England. The annual NH Highland Games and Festival features traditional heavy athletic competitions you don’t see on NESN every day, like the caber toss. Cheer your favorite team, find your clan, watch sheepdog trials, hear pipe bands. There are Scottish goods to purchase and foods and whiskies to sample. Don’t be afraid of the haggis hurling: It’s code for corn hole.

L.L. Bean Flagship Grand Opening | Freeport, ME

On Friday, September 18, L.L. Bean will unveil its reimagined flagship store campus, and the Grand Opening celebration continues not only through this weekend but straight through October. Don’t miss the free outdoor concert in Discovery Park by country artist Kip Moore Friday evening at 7 p.m., plus your chance to be among the first to see the flagship store’s new multilevel trout pond.

Fluff Festival | Somerville, MA

Archibald Query of Somerville, Massachusetts, created Marshmallow Fluff in 1917, and more than a century later, this Boston suburb is still celebrating his culinary achievement. At the 21st annual Fluff Festival on Saturday, September 19, you can get yourself into some pretty sticky situations … even if you don’t participate in the Fluff Hairdo contest. Bring wet wipes, and indulge in a sweet taste of history.

The British Invasion | Stowe, VT

British motorcar collectors and fans converge upon the Stowe Special Events Field from Friday, September 18, through Sunday, September 20, for a fun-filled fall weekend of all things English. The British Invasion attracts more than 500 cars each year, and parking fees benefit the American Cancer Society.

Books by the Sea | Yarmouth, MA

If a “readaway” has been on your bucket list all year, it’s time to make your dream nonfiction. Cape Cod’s Red Jacket Blue Water Resort hosts its inaugural Books by the Sea literary retreat this weekend, featuring authors Hannah Selinger (Valley of the Moms), Jeanette Settembre (Little Red Flags), and Meg Mitchell Moore (Down with the Shipmans). Book lovers can choose from two immersive packages, The Paperback Experience (starting at $782) or The Hardcover Experience (starting at $1.045).

Weekend of September 26-27, 2026

Burke Fall Festival | East Burke, VT

The 37th annual Burke Fall Festival kicks off at 10 a.m. on Saturday, September 26, with a festive parade. This year’s theme is Wild Kingdom. Here in Vermont’s remote Northeast Kingdom, fall color arrives early, and this annual tradition brings folks from near and far together for seasonal treats like apple cider slushies, music and entertainment, horse-drawn wagon rides, and the chaotic thrill of Rubber Ducky Races and Cow Plop Bingo. There’s a craft fair featuring more than 75 vendors, a petting zoo, free ice cream for kids, and much more.

WaterFire | Providence, RI

If you’ve never experienced WaterFire, you really must go this fall. On Saturday, September 26, from sunset until midnight, Providence’s signature event, which I’ve often called the most romantic free thing you can do in New England, turns the city into a living work of art. This moving combination of rivers and bonfires, always accompanied by an ethereal soundtrack selected for one evening alone, is pure enchantment and worthy of a trip.

Colonial Faire and Fife & Drum Muster | Sudbury, MA

Celebrate America’s big 250th birthday! Step into a time machine on Saturday, September 26, when the grounds of historic Longfellow’s Wayside Inn host a Colonial Faire and Fife & Drum Muster. From craft demos to contra dancing, it’s an immersive day of celebrating New England’s heritage, complete with a Grand Parade and individual performances by more than two dozen fife and drum corps from throughout the Northeast. Admission and parking are free.

Fun Sized A Tiny Public Art Festival | Northampton, MA

For the weekend of September 26–27, Downtown Northampton becomes a walkable gallery filled with mini works of art. Fun Sized A Tiny Public Art Festival features works by more than a dozen contemporary creators. Go on Saturday if you can, when the installation aligns with Jazz Fest Day, featuring free performances citywide.

New England BIPOC Fest | Portsmouth, NH

Strawbery Banke provides the setting for the New England BIPOC Fest on Sunday, September 27, and you’re invited to experience the joy and exuberance of people from all backgrounds coming together to celebrate the music, art, food, and culture of Black, Indigenous, and People of Color (BIPOC) communities.

Settlers Green Fall Festival | North Conway, NH

From 10 a.m. until 2 p.m. on Saturday, September 26, families are invited to a free fall festival, where even the apples and cider are complimentary (while supplies last!). The Settlers Green Fall Festival is held in the White Mountains hub town of North Conway, where we’re taking Yankee readers for a Weekend Away in our September/October issue. Your kids will love painting pumpkins, petting farm animals, and pedaling tractors, and you’ll love the live music and shopping deals at this destination for tax-free outlet shopping.

New This Month in New England

The Honor Summit | Mount Washington, NH

As we mark the 25th anniversary of 9/11, the Granite Springs Foundation is bringing to life the Honor Summit, a moving installation that will shine two towers of light from the summit of Mount Washington, New England’s highest peak, toward the heavens. The beams will be visible September 9–12 from locations as far as 135 miles away from the mountain. The Honor Summit is also a fundraising effort, with donations supporting four nonprofits that help veterans access vital emotional and mental health resources.

Mystic Pizza: A New Musical | Elmira, NY, and Waterbury, CT

The film that launched Julia Roberts’s career—based on the story inspired by a Mystic, Connecticut, pizza joint—has been reimagined for the stage. The national tour of Mystic Pizza: A New Musical kicks off this month in Elmira, New York, where it runs September 26–27 at the Clemens Center. You can also get tickets now for the tour’s only New England stop, October 2–4 at the Palace Theatre in Waterbury, Connecticut. And don’t forget—you can still enjoy a “slice of heaven” at the original Mystic Pizza in Connecticut!

Hawksmoor | Boston, MA

Boston has a new steakhouse, an import from London, and you can be among the first to salivate over not only charcoal-cooked meats but sustainable seafood and sticky toffee pudding! Hawksmoor, overlooking the Fort Point Channel, officially opens September 8.

Mohegan Sun Self-Guided Cultural Tour | Uncasville, CT

We took you to Mohegan Sun for a Weekend Away in Yankee‘s Jan/Feb issue, and this fall, there’s an all-new reason to visit this dynamic casino resort. Experience the stories and traditions of the Mohegan Tribe via a self-guided, QR-code-powered Mohegan Cultural Tour. Narrated by Mohegan Elder and former Mohegan Tribal Chairman Bruce “Two Dogs” Bozsum, the journey is filled with Indigenous wisdom and history, now woven throughout the property. You’ll also hear from Lynn Malerba (Chief Many Hearts), the current Lifetime Chief of the Mohegan Tribe and the first woman to hold this role in more than 300 years.

September’s Best Deals

Save on Fall Road Trip Treats from Effie’s Homemade

Yankee Food Award winner Effie’s Homemade crafts oatcakes and many varieties of biscuits that are beautifully boxed and perfect for fall cheese boards, picnics, and road trip snacking. This month, as a special offer for our Yankee readers, you can stock up on your favorite made-in-Massachusetts treats and save 20% with the discount code Kim20.

Stay at the Topnotch Resort | Stowe, VT

The Stowe-liage Foliage Package (from $324) at Vermont’s Topnotch Resort includes a $100 nightly resort credit, essentially paying for your meals while you enjoy golden mountain views from the heated outdoor pool or the pickleball courts. This deal is available for travel dates through September 30 and again October 17–December 20.

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

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