A Local’s Advice on How to Have the Best New England Fall Vacation

New England’s fall season is the stuff of legends. Between the perspiration of summer behind you and the ice of winter ahead, the air whispers with a soft wind.

It turns into a vibrant spectacle, with trees transforming from emerald green to burnt orange, crimson, amber, and deep purple. It’s a place where holiday cheer is near mandatory from Labor Day through Christmas, and where, once Sept. 1 comes around, hot apple cider flows like a river.

I’m not just waxing poetic about another destination. I’m speaking from experience as someone who grew up in Rhode Island, went to college in Boston, learned to ski in Vermont, and even married a Mainer. New England is what I know, and I’m happy to share some expert tips so you can explore this glorious region at its best.

What to Know Before You Go to New England in the Fall

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Though we’re speaking about New England as a singular place in this story, it is by no means a monolith. New England is made up of more than 70,000 square miles, home to more than 14 million people, and includes the states of Connecticut, Rhode Island, Massachusetts, New Hampshire, Vermont, and Maine. That means, before you decide on a New England vacation, you should first determine if you want to visit a particular state or take a road trip through multiple destinations.

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The drive from the capital of Connecticut (Hartford) to the capital of Maine (Augusta) is a four-hour straight shot, but that won’t allow you to meander as you should through the area. Your best bet is to pick a destination (for example, Newport, Rhode Island; Salem, Massachusetts; or Stowe, Vermont) or route that will take you to some of the most pristine landscapes (think: New Hampshire’s Kancamagus Highway). Or, if you’re outdoorsy, you can hike a portion of the Appalachian Trail, which snakes through Connecticut, Massachusetts, Vermont, New Hampshire, and Maine.

It’s also important to consider the varied weather. Day by day and state by state, things can change in a moment. Be prepared for chilly mornings, warm afternoons, and even colder nights. Pack in layers and bring gloves and a hat. You won’t regret it.

Best Things to Do in New England in the Fall

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New England is packed with things to do all year long, but fall is a prime time to visit as it’s a semi-shoulder season for most communities — just after the summer surge for beach towns and before ski season for the mountains. That means you can explore many popular spots with thinner crowds.

Head to places like Boston to snag hard-to-get reservations at the hottest hotels and restaurants like The Newbury, XV Beacon Hotel, and The Langham (all top choices in Travel + Leisure‘s 2022 World’s Best Awards). While there, check out The Freedom Trail to both soak in some history and see as much of the city in one go.

PGIAM/GETTY IMAGESRICHARD MANDELKORN/COURTESY OF THE LANGHAM, BOSTON

Another can’t-miss — albeit cliche — New England fall activity is apple picking. There are hundreds of apple orchards sprinkled around New England, but some of the best can be found in New Hampshire. Spots like Alyson’s Orchard in Walpole offer hundreds of acres to explore, along with farm animals to pet and game areas to play in. Riverview Farm in Plainfield provides the same picking experience, but with the added bonus of a seasonal corn maze.

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Fall in New England is also a perfect time for a hike, thanks to the pristine weather. Again, you can hop on or off the Appalachian Trail at dozens of entrance points or make your way to Maine to visit Acadia National Park, the only national park in New England. With more than 150 miles of trails, it’s a place where you can spend a week in and never be bored.

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Of course, there’s also leaf peeping, but that’s worthy of its own section, so keep reading.

Festivals in New EnglandESSDRAS M SUAREZ/THE BOSTON GLOBE/GETTY IMAGES

Fall is harvest season in New England, which means there are plenty of fairs to go along with it. This includes the New Hampshire Pumpkin Festival in downtown Laconia, the Topsfield Fair in Topsfield, Massachusetts, the Deerfield Fair (which proudly weighed the largest pumpkin recorded in the U.S. in 2018) in Deerfield, New Hampshire, and more. Odds are, you’ll find at least a fair or two in the state you’re visiting.

New England Fall Foliage

Leaf peeping is a sport in New England, won by all who get to enjoy it. The prime time to see the leaves at their peak is toward the end of September and into early October. You can also track the change in real-time with this handy tool from NewEngland.com. It’s a bit dependent on location, as the leaves in northern Maine will most certainly change faster than southern Rhode Island, so after picking your destination, check in for the correct timetable.

As for where to go, you’re spoiled for choice. A few favorites include the quaint community of Camden, Maine; the more bustling area of Portsmouth, New Hampshire; down to the adorable Old Lyme, Connecticut; and the aforementioned Kancamagus Highway, New Hampshire, which is ideal for those who want to feel like they’re driving through a kaleidoscope. Check out our picks for the best places to go leaf peeping in New England.

Hotels in New EnglandCOURTESY OF THE WAUWINET

New England’s charm certainly extends to its hotels and bed-and-breakfasts. Here’s a small selection to choose from, including several that made T+L’s 2022 World’s Best Awards list.

Pickering House Inn, Wolfeboro, New Hampshire

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The Pickering House Inn is a perfect mix of old meets new. The boutique hotel sits in a home built in 1813, but was lovingly restored during a two-year renovation. Guests can expect many of the perks of a bed-and-breakfast, including breakfast, one-of-a-kind accommodations, and more.

Ocean House, Westerly, Rhode Island

The historic Ocean House is ready to cater to your every desire, from fine-dining eateries and beachside walks to wellness experiences and pet-friendly amenities. It’s a time-honored favorite tucked away in one of the most stunning corners of New England, and will absolutely make you feel like Rhode Island royalty.

The Wauwinet, Nantucket, Massachusetts

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For another coastal getaway, book a stay at The Wauwinet, a Relais & Châteaux property. The hotel, which has been welcoming guests since 1875, offers private beach access, tennis courts, fine dining, complimentary bikes, and more, so you can get out and explore the surroundings.

The Wanderer, Kennebunk, Maine

Looking for something a little different? Book a stay at The Wanderer, made up of small, Instagram-worthy cottages. Note: The hotel is only open until the end of October, so make sure to time your trip correctly.

Trapp Family Lodge, Stowe, Vermont