Autumn road trip in New England

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In the mood for a pampering holiday? Throw in some cool historical attractions? Immerse yourself in art? Then you’re ready for a fall road trip to your New England bed and breakfast. Do it during leaf peeping season and you’ll hug yourself with gratitude.

My travel companion and I timed our two-week New England trip for warm weather and the peak of foliage peeping season: mid-September through early November. These leaves are the pinnacle of art, as their natural wonders bathe travelers in lime green, lime yellow and chocolate fronds – sometimes on the same leaf. For two weeks we enjoyed radiant sunshine and temperatures in the high 60s and low 70s.

When booking rooms, my goal was to find affordable accommodations with parking, breakfast, and charm. I’ve found some quaint Victorian B&Bs that artistically display plump pumpkins and potted mums from burgundy red to snowy white to decorate their entryways. Not all accommodations were Victorian, served breakfast and were reasonably priced, but they all had some of these elements.

Newport Rhode Island
Newport Rhode Island. Image from Canva

Newport, Rhode Island

In Newport, Rhode Island, we stayed at Savvy tenant, one block from Bellevue Street Mansions. We immersed ourselves in seeing Newport Mansion, highlighted by a tour of The Breakers, the original Vanderbilt mansion modeled on Italian Renaissance palaces.

crab- boiled, grilled, Newburgh-ed, quesadilla-ed, risotto-ed, flatbread, bisque-ed or cabbage – is an important taste of East Coast flavor. The entire sampling included forays into Newport Marsa Restaurant And the White Horse Pubthe oldest operating restaurant in the United States.

Autumn Road on Cape Cod
Autumn Road on Cape Cod. Image from Canva

Cape Cod to Salem, Massachusetts

Cape Cod, Massachusetts, was a short drive from Newport, and we stayed in a budget hotel Sandwich Inn, It’s not Victorian, but it met the breakfast and parking goals. We took the car to the tip of the Outer Cape to Race Point, where you can climb the lighthouse stairs for a great view. Luxurious Chatham Bars Inn It is a luxurious resort with another sweeping view and delicious dinner.

It was an easy trip south on Cape Town to Hyannisport before Heading to Boston. Hyannis is home to the Kennedy Historical Complex, and although the Kennedy family still uses the property, a visit to the John F. Kennedy Hyannis Museum is accessible and memorable.

Fair and bed and breakfast don’t belong in the same sentence when applied to Boston, but we stayed in the heart of Boston in Newbury Guest House. Located in Boston’s Back Bay district, this historic guest house features an on-site bakery, Patisserie on Newbury. We had a delicious lunch at Cheers where it was fun to look at the replica of the set used to film the TV series.

The lobster men at Lobster Wharf were unloading their boats, and the tuna fishermen were hoisting their huge tuna catches to the processing plant in Gloucester, Massachusetts. We had the rare opportunity to witness the art of negotiating the best price per pound between Wicked Tuna TV. Show tuna processor and fishermen.

Salem, Mass, was in full swing with its haunted events – all throughout the month of October. Attendees dressed in witch costumes dance and sing their way through the festivities. A trolley tour of the city revealed the seven-gabled Nathaniel Hawthorne House among the historically preserved homes.

Kennebunkport lobster boats.
Kennebunkport lobster boats. Image from Canva

Kennebunkport, Maine

Next was Kennebunkport, Maine, which offers an easy view of Bush’s prominent properties on the peninsula. Lunch in Arundel Wharf Restaurant Featuring thick, homemade chips, the Colony Hotel is worth a visit for a good meal and old-world hospitality. The hike down the slope of The Marginal Way begins at Perkins Cove in Ogunquit, ME (adjacent to Wells) and is breezy and rocky – like Maine itself.

We stayed at Wells (near Kennebunk) for a surprisingly reasonable price Holiday Guest HouseIt is a luxuriously decorated Victorian home with an attractive host, vertical ship stairs and a gourmet breakfast.

Find other great hotels in Kennebunkport, Maine here

The Victorian bed and breakfast brought East Coast appeal literally into our bedroom, often via narrow stairs. Call them ship stairs or Victorian stairs. Call it what you want, as long as you’re prepared to deal with it when visiting Victorian homes on the East Coast. The stairs are often narrow and steep in these luxury homes. It may take a while to get to the gym, but it’s worth climbing those steep slopes to visit the homes.

Berries are a pride who, and I blame the dinner at Maine Diner for leaving me with a taste for blueberries. At various locations, I had blueberry pie, muffins, pies, and pie. I can confirm that Maine should be proud.

Bar Harbor Maine
(Bar Harbor, Maine). Image from Canva

(Bar Harbor, Maine).

We passed salt marshes, flowering meadows with yellow mustard and red cranberries, the occasional wild turkey and classic homes as we drove down Highway 1 to Bar Harbor, Michigan. One step you’ll want to do is at the end of Bridge Street leading to Bar Island – when the tide is low. The other is on a high rocky beach that begins in front of the Eternal Bar Harbor Inn. The final trail takes you to what New Englanders call “cottages,” even though they are mansions. Since they usually serve as second homes, they may even serve as cottages to some.

Acadia National Park on Mount Desert Island in Bar Harbor fills the air with tart green mixed with salty sea air. Hike or take the free bus to watch the foliage turn mustard yellow, burnt red and crimson red on Cadillac Mountain, which offers stunning views of the icy landscape. Free parking is available, so make time for lunch at Jordan Pond, a historic stop for tea and popovers.

You could smell the lobster boiling in huge pots outdoors on the Bar Harbor dock, so I needed to enjoy myself again. This time with delicious boiled lobster. More indulgence came from staying at a captivating and affordable hotel Ivy Manor Inn. We hiked around Long Pond, where you can lose yourself in the beauty and solitude of nature.

To get the full dose of fall colors, we headed up the Kancamagus Highway to our goal of New Hampshire’s White Mountains. Because it’s a two-lane highway, the trees tower over our heads, enveloping us in a blanket of lime green, tangerine orange, and ruby ​​red spots stitched together in threads of blazing sunshine. It was a warm embrace.

(North Conway New Hampshire).
(North Conway, New Hampshire). Image from Canva

New Hampshire

Orvis’s headquarters in Manchester, Vermont, covered our long haul as we made our way to North Bennington, VT. Since Orvis has given my man the opportunity to practice casting a fly in the pond, how could we not stop?

We met friends at Merrill Farm Inn On the Saco River in North Conway when we traveled to New Hampshire. Chocolate chip cookies were coming out of the oven when we arrived, and we might have been tempted by the smell if the white-board ambiance of this inn hadn’t already drawn us in. We stayed for several days to enjoy catching up with our friends.

We then took the Down East Highway, where we passed the Coach Stop Inn, another historic place to stay. The highway is dotted with many antique shops and cemeteries, bearing witness to centuries of ancestor burials.

Bennington Vermont
Bennington Vermont. Image from Canva

Bennington, Vermont

We traveled to Bennington, VT, to see my partner’s grandparents’ house. Cheese, crackers and cookies greeted us when we arrived at the reasonable prices Eddington House. This inn (with narrow stairs, of course) features interesting antiques and serves a hearty breakfast. Old First Church includes a cemetery that includes the burial site of Robert Frost and a towering monument to the Green Mountain Boys, who fought in the Revolutionary War.

We crossed the Henry Covered Bridge to discover that the Henry House, so cherished by the lover’s family, is more than worthy of being placed on the National Register of Historic Places. Its spread is ornate, its river bed is stocked with trout, and the property is meticulously maintained by the owners who enthusiastically showed us the house and grounds. The house, built in 1769, is one of the oldest surviving homes in Vermont, and now hosts weddings and events.

As we departed via Highway 2 (Mohawk Road), multi-colored foliage floated up from their final resting places, bidding us farewell. I found myself singing John Denver’s “Annie’s Song”: “You fill my senses like a night in a wood.” This journey through history awakened our senses with forests filled with vibrant, wind-blown foliage, the allure of waterways and the scent of warm B&B buns.

Fall of New England
Henry House Sign and Bridge. Photography by Marcia McGreevy Lewis

Where to Stay on a New England Fall Road Trip

You'll embrace your gratitude with this New England road trip that includes historic towns, charming inns, and fun excursions. #newenglandfall #newenglandroadtrip

New England Fall Trip Expeditions

  • Newport, Rhode Island: The Breakers, Vanderbilt Mansion, and The White Horse Tavern
  • Cape Cod, Massachusetts: Drive to Race Point on the outer headland to a view of the lighthouse
  • Hyannisport, MA: John F. Kennedy Hyannis Museum
  • Boston, Massachusetts: Lunch at Cheers Bar
  • Gloucester, Massachusetts: Lobster Wharf to see lobster and tuna boats
  • Kennebunkport, ME: Cliffside Road
  • New Hampshire: White Mountains for leaf peeping
  • North Bennington, Virginia: Henry’s Home and Old First Church of Robert Frost’s burial site.

Author’s biography: Marcia McGreevey Lewis (she/her) lives in Seattle and is a retired Washington newspaper writer. She has written for literary journals, magazines, travel websites, and books such as Chicken Soup for the Soul. You can reach her on Facebook and Instagram: marcialewis25, Twitter: @McGreevyLewis, and Linkedin: marcia-lewis.


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