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. 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 five September weekends, plus the inside scoop on some of early fall’s best deals.

Labor Day Weekend, August 31-September 2, 2024

Garlic Town U.S.A. | Bennington, VT

Start your Labor Day weekend in New England at a destination that comes to life just one day each year: Garlic Town U.S.A. On Saturday, August 31, more than 100 purveyors of garlicky goods will gather in downtown Bennington, Vermont, to tantalize your tastebuds (yes, there will garlic ice cream). This beloved community festival is about more than the venerable bulb, though. Bands play all day, there are games and activities for kids and adults, and the bar tent serves up Garlic Bloody Marys.

Silent Disco White Party at Aquila’s Nest Vineyards | Newtown, CT

On Saturday evening, August 31, dress in white and ring in September at a Silent Disco (purchase tickets online). You’ll be provided with wireless headphones and can choose your own music channel, which sounds like the makings of a laugh-filled party even before you add wine. But you really should try the sustainably sourced snack and wine pairing flight at Aquila’s Nest Vineyards, where creative events like this are on the calendar throughout the summer-into-fall season (and beyond).

King Richard’s Faire | Carver, MA

New England’s largest and longest-running Renaissance festival opens this weekend for its 43rd season. Can’t get there August 31-September 2? You’ll have a realm of opportunities to visit King Richard’s Faire on weekends and Monday holidays through October 20. Do go in costume… and do devour a two-pound turkey leg.

Weekend of September 7-8, 2024

Guilford Porchfest | Guilford, CT

Got a lawn chair? Then, you have everything you need to attend Guilford Porchfest. On Saturday, September 7, porches throughout this Connecticut shoreline community will host free live performances by locals. It’s a celebration of just how much talent resides within this town known for its thriving arts scene.

Weekend of September 14-15, 2024

The Big E | Springfield, MA

It’s opening weekend for New England’s mega-fair, The Big E, which promises non-stop fun from September 13-29. 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 Big E’s most tantalizing attraction is over-the-top food, from deep-fried Kool Aid to giant cream puffs. New this year: Student Prince, Springfield’s nearly 90-year-old German restaurant, serves up favorites at their Wurst Haus.

Maine Open Lighthouse Day | various locations

On Maine Open Lighthouse Day, Saturday, September 14, 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 300 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 21-22, 2024

NH Highland Games & Festival | Lincoln, NH

From September 20-22, all things Scottish are a short drive away if you live in New England. The annual NH Highland Games & 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.

WaterFire | Providence, RI

If you’ve never experienced WaterFire, you really must go. You have one shot this month: Saturday, September 21, from sunset until 11 p.m. I learned recently that Providence’s signature event, which I’ve often called the most romantic free thing you can do in New England, is facing a funding shortfall. 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… and your support.

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 Fluff Festivalon Saturday, September 21, 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.

Weekend of September 28-29, 2024

Burke Fall Festival | East Burke, VT

Celebrating 35 years in 2024, the Burke Fall Festival kicks off at 10 a.m. on Saturday, September 28, with a parade with a “Great Outdoors” theme. 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, 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.

Colonial Faire and Fife & Drum Muster | Sudbury, MA

Don’t wait until 2026 to celebrate America’s big 250th birthday. Step into a time machine on Saturday, September 28, when the grounds of historic Longfellow’s Wayside Inn host a Colonial Faire and Fife & Drum Muster. From craft demos to contradancing, it’s an immersive day of celebrating New England’s heritage, complete with a Grand Parade and individual performances by 25 fife and drum corps from throughout the Northeast.

New This Month in New England

Harry Potter: The Exhibition | Cambridge, MA

It’s Boston’s turn to welcome a touring exhibition that has captivated millions of Harry Potter fans worldwide. Opening September 13 at CambridgeSide, Harry Potter: The Exhibition celebrates the characters, settings, and stories that leapt from books to the silver screen to the Broadway stage. You’ll see authentic movie and theatrical costumes and props, experience immersive environments, and engage with the magic through everything from photo ops to Quidditch practice. The exhibition runs through January 5, and tickets can be purchased online. Celebrate Opening Day in Boston on September 13 with tickets for 9 ¾… $9.75! 

September’s Best Travel Deals

Save 30% at Getaway | Two New England locations

The cabins at Getaway resorts in Connecticut and New Hampshire are your own little retreats in the midst of nature, and September is one of the most dramatic times to experience changes in the landscape. Book by September 3 for stays through September 26, and you’ll save 30% on your reservation with code BACKTONATURE. Can’t escape in September? Book your October or November stay by September 3 and save 20% with code VIBESHIFT.

AWOL Stowe Grand Opening Promotion | Stowe, VT

Through September 19, AWOL Stowe is celebrating its debut with special room rates for you. Book online or by calling 802-277-6200, and you’ll also receive two complimentary cocktails and an exclusive local gift. “Untamed luxury” is AWOL’s objective, and to that end… you can add a three-course dinner in the forest, prepared by a private chef, to your getaway experience.

Lobzilla at Student Prince | Springfield, MA

Twin lobsters for $26? That’s a steal for seafood lovers! The Lobzilla promotion at Springfield’s famous German restaurant, Student Prince, is available on Thursdays and Fridays, but you must call 413-734-7475 to make a dining reservation and pre-order lobsters.

Yankee Out & About This Fall

Staying or dining at Castle Hill Inn in Newport, Rhode Island, on September 23 or 24? You might catch a glimpse of our Weekends with Yankee cast and crew filming a segment for Season 9 of our PBS television show.

On Saturday, September 28, join us in remembering long-time Yankee writer and columnist Edie Clark at a reading of her works. Yankee editor Mel Allen will emcee this event, which begins at 4 p.m. at the Unitarian Universalist Church at 25 Main Street in Peterborough, New Hampshire. The readers will be writers whose lives intersected with Clark’s—including the nationally famous naturalist Sy Montgomery. “Her writing is what really defined Edie to her readers, and we want to give her a final sendoff,” Allen says. Her books, including previously out-of-print editions, will be available for purchase.

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.