September in New England: Best Events and Travel Deals
As summer yields to fall, spend September weekends experiencing the best of both seasons. Here’s your guide to fun events and escapes in New England this month.
By Kim Knox Beckius|Aug 21 2025|
The Big E, New England's largest fair, showcases the awesomeness of all six states over the course of 17 days in September.
Photo Credit: Christopher Evans / The Big ESeptember 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 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.
Weekend of September 6-7, 2025
Outlaw Music Festival | Bangor, ME; Hartford, CT; and Mansfield, MA
Willie Nelson, Bob Dylan, Sheryl Crow, and a host of other talents will take the stage as the Outlaw Music Festival makes three New England stops in three days, starting on Friday, September 5, at the Maine Savings Amphiteater in Bangor. Catch this 10th-anniversary tour at the Xfinity Theatre in Hartford on Saturday or the Xfinity Center in Mansfield on Sunday before these troubadors are on the road again.
King Richard’s Faire | Carver, MA
New England’s largest and longest-running Renaissance festival is in the midst of its 44th season, and you’ll have a realm of opportunities to visit King Richard’s Faire on weekends and Monday holidays through October 19. Do go in costume … and do devour a two-pound turkey leg.
Guilford Porchfest | Guilford, CT
Got a lawn chair? Then, you have everything you need to attend Guilford Porchfest. On Saturday, September 6, 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 13-14, 2025
Photo Credit : Christopher Evans / The Big E
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 12-28. Yes, there are agricultural competitions, concerts (I am irrationally excited that Tonic is playing a free show on September 12), 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: Big E Bike Night on Thursday, September 25, from 4 to 8 p.m.
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 12, through Sunday, September 14, meet cast members including Scott Patterson (Luke!), compete in trivia and other contests, make crafts, attend a harvest festival, 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.
Photo Credit : Kim Knox Beckius
Maine Open Lighthouse Day | various locations
On Maine Open Lighthouse Day, Saturday, September 13, 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 20-21, 2025
Photo Credit : NHSCOT
NH Highland Games & Festival | Lincoln, NH
From September 19-21, 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.
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 20th annual Fluff Festival on Saturday, September 20, 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 17, through Sunday, September 21, for a fun-filled fall weekend of all things English. The British Invasion attracts more than 600 cars each year, and parking fees benefit the American Cancer Society.
Weekend of September 27-28, 2025
Burke Fall Festival | East Burke, VT
The 36th annual Burke Fall Festival kicks off at 10 a.m. on Saturday, September 27, with a festive parade. This year’s theme is Spokes & Flakes. 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.
Panda Fest | Hartford, CT
Head to Mortensen Riverfront Plaza on Saturday and Sunday, September 27 and 28, as Hartford welcomes Panda Fest for the first time. Tickets, which include two free gifts, can be purchased online for this celebration of Asian culture and cuisine featuring more than 50 food vendors, music and dance performances, local makers, Chinese acrobats, and photo ops with inflatable pandas.
WaterFire | Providence, RI
If you’ve never experienced WaterFire, you really must go during this 30th-anniversary season. You have one shot this month: Saturday, September 27, from sunset until midnight. Providence’s signature event, which I’ve often called the most romantic free thing you can do in New England, has faced a funding shortfall in recent years. 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.
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 27, 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 25 fife and drum corps from throughout the Northeast. Admission and parking are free.
New This Month in New England
Driving Tours at West Place Animal Sanctuary | Tiverton, RI
Meet rescued farm animals and enjoy the beauty of a historic Farm Coast property, all from the comfort of the CRU by Club Car: a quiet, eco-friendly, five-passenger electric vehicle. These new West Place Animal Sanctuary Driving Tours make the grounds accessible to all visitors, including those with mobility challenges. Reserve your fully guided experience online.
Photo Credit : Paradigm Escape Rooms
An Outdoor Mystery Treasure Hunt | Newport, RI
Fall feels like the season to play detective, and now you can immerse yourself in an outdoor mystery adventure with Newport’s colonial and Gilded Age history as your captivating backdrop. Paradigm Escape Rooms’ new outdoor game, A Sea City’s Secret: The Unsolved Case of the Harrow Family, invites you to uncover a fictional family’s long-buried secrets and locate a hidden treasure. Using your smartphone (and your own smarts), you’ll follow a 1.5-mile walking loop through the historic city, solving puzzles and finding clues. Book your experience online—it’s suitable for ages 10 and up and groups as large as eight people.
September’s Best Travel Deals
A Fall Kickback | Stowe, VT
The Stowe-liage Foliage Package (from $279) 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 October 14-November 30.
Lobzilla at Student Prince | Springfield, MA
Twin lobsters for $39.99? That’s a steal for seafood lovers! The Lobzilla promotion at Springfield’s famous German restaurant, Student Prince, is available on Wednesdays and Thursdays, but you must call 413-734-7475 to make a dining reservation and pre-order lobsters.
Yankee Out & About This Fall
Yankee’s Free Fall Foliage Photography Webinar
Capture the magic of autumn with tips from photographer and Yankee foliage expert Jim Salge. In this live session at 7 p.m. Eastern on Tuesday, September 16, Jim will share his 2025 fall foliage forecast, explore what makes the season so enchanting, and offer advice on getting your most stunning shots ever. Whether you’re a seasoned photographer or a casual leaf peeper, you’ll come away inspired and ready to make the most of the season. Register now!
Meet Mel Allen
Yankee‘s long-time editor, now editor at large, Mel Allen has a new book, Here in New England, just out, and you can catch Mel at one of the many book-tour events he has scheduled this fall. We’re particularly excited about Mel’s talk at The Music Hall Lounge in Portsmouth, New Hampshire, on the evening of September 25. Reserve your tickets, which include a signed book, and join us!
Harvest Party
Get your tickets now, and also join us on October 16 for the Boston Public Market’s Harvest Party. This year, the nonprofit’s annual fundraiser celebrates the market’s 10th birthday, and Yankee is pleased to be a media sponsor for the event.
