New England Fall Road Trip

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In the mood for a pampered getaway? Throw in some fascinating historical sights? Immerse yourself in art? Then you’re ready for a bed-and-breakfast New England fall road trip. Time it during leaf-peeping season and you’ll hug yourself in gratitude.

My traveling companion and I timed our two-week New England drive for warm weather and the peak of leaf-peeping season: mid-September through early November. Those leaves are the height of art, as their natural wonder immerses travelers in lime green, lemon yellow and chocolate fronds—sometimes on the same leaf. We reveled for two weeks in radiant sunshine and temperatures in the high 60s and low 70s.

When booking rooms, my goal was to find reasonably priced accommodations with parking, breakfast and charm. I found some enticing Victorian Bed and Breakfasts artfully displaying plump pumpkins and pots of mums from burgundy red to snow white decorating their doorways. Not all accommodations were Victorian, served breakfast and were reasonably priced, but all had some of those elements.

Newport, Rhode Island

In Newport, Rhode Island, we stayed at The Artful Lodger, one block from the Bellevue Avenue mansions. We immersed ourselves in Newport’s mansion viewing, highlighted by a tour of The Breakers, an original Vanderbilt manor modeled on Italian Renaissance palaces.

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Lobster–boiled, broiled, Newberg-ed, quesadilla-ed, risotto-ed, flatbread-ed, bisque-ed or rolled—is an important taste of East Coast flavor. Sampling it all included forays to Newport’s Mooring Restaurant and the White Horse Tavern, the oldest operating restaurant in the US.

Autumn road on Cape Cod. Image from Canva

Cape Cod to Salem, Massachusetts

Cape Cod, Mass., was an easy drive from Newport, and we stayed at the economical Sandwich Inn, which is not Victorian, but it met the goals of breakfast and parking. We took the drive to the tip of the Outer Cape to Race Point, where you can climb the lighthouse stairs for a great view. The stately Chatham Bars Inn is a luxury resort with another sweeping view and a tasty dinner.

It was an easy drive south on the Cape to Hyannisport before heading to Boston. Hyannis is home to the historic Kennedy Compound, and though the Kennedy family still uses the property, visiting the John F. Kennedy Hyannis Museum is available and memorable.

Reasonable and bed and breakfast don’t belong in the same sentence when applied to Boston, but we did stay in the heart of Boston at the Newbury Guest House. This historic guest house is located in Boston’s Back Bay district and features an on-site bakery, Patisserie on Newbury. We had a tasty lunch at Cheers where it was fun to glimpse the replica of the set used to film the TV series.

Lobstermen at Lobster Wharf were unloading their boats, and tuna fishermen were hoisting their massive tuna catch up to the processing plant in Gloucester, Mass. We had the rare opportunity to witness the art of negotiation for the best price per pound between the Wicked Tuna TV show tuna processor and the fishermen.

Salem, Mass., was in full swing with its Haunted Happenings–all of October. Attendees in witch costumes dance and sing their way through the festivities. A trolley tour of the town revealed Nathaniel Hawthorne’s House of Seven Gables among the historically preserved homes.

Kennebunkport lobster boats. Image from Canva

Kennebunkport, Maine

Next was Kennebunkport, Maine, which provides an easy view of the Bush properties jutting out on a peninsula. Lunch at Arundel Wharf Restaurant featured thick homemade potato chips, and the Colony Hotel is worth a visit for a good meal and old-world graciousness. A stroll down The Marginal Way cliff walk starts at Perkins Cove in Ogunquit, ME (adjacent to Wells) and is breezy and rocky—like Maine itself.

We stayed in Wells (close to Kennebunk) at the surprisingly affordable Holiday Guest House, a sumptuously decorated Victorian home with an engaging host, vertical ship’s stairs and an appetizing breakfast.

Find other great hotels in Kennebunkport, Maine here

Victorian bed and breakfasts brought the allure of the East Coast literally into our bedroom, often via narrow stairs. Call them ship’s stairs or Victorian stairs. Call them whatever you want, as long as you’re prepared to tackle them when visiting Victorian homes on the East Coast. Stairs are often tight and steep in those stately homes. It might take a little hitting the gym, but it’s worth climbing those precipitous slopes to visit the homes.

Blueberries are the pride of Maine, and I blame dinner at the Maine Diner for jettisoning me into blueberry tasting. At various locations, I had blueberry pie, muffins, pancakes and pie. I can verify that Maine should be proud.

Bar Harbor, Maine

We passed salt bogs, meadows blooming with mustard yellow and cranberry red flora, the occasional wild turkey and classic homes as we drove Highway 1 to Bar Harbor, ME. One walk you’ll want to take is at the end of Bridge Street to Bar Island—when the tide is low. The other is on a rocky high beach that starts in front of the timeless Bar Harbor Inn. The latter walk takes you by what New Englanders call “cottages,” though they’re mansions. Since they’re usually second homes, maybe they are cottages to some.

Acadia National Park on Bar Harbor’s Mount Desert Island fills the air with pungent evergreens mixed with salty sea air. Hike the trails or ride the free bus to see the leaves turning mustard yellow, burnt umber and scarlet red on Cadillac Mountain, which offers magnificent views of the glaciated landscape. Parking is free, so take time for lunch at Jordan Pond, an historic stop for tea with popovers.

You can smell lobsters boiling in huge open-air pots on the wharf in Bar Harbor, so I needed to indulge myself again. This time with luscious boiled lobster. More indulgence came from staying at the captivating yet reasonably priced Ivy Manor Inn. We walked around Long Pond, where you can lose yourself in nature’s beauty and solitude.

To get the full dose of fall colors, we headed over the Kancamagus Highway to reach our goal of the White Mountains of New Hampshire. Because it’s a two-lane highway, the trees are overhead, wrapping us in a quilt of lime green, tangerine orange and ruby red patches stitched together with threads of blazing sunshine. It was a sensational embrace of warmth.

New Hampshire

Orvis headquarters in Manchester, Vermont, broke up our long haul as we wove our way to North Bennington, VT. Since Orvis provided an opportunity for my guy to practice his fly casting in its pond, how could we not stop?

We met friends at Merrill Farm Inn on the Saco River in North Conway when we drove into NH. The chocolate chip cookies were coming out of the oven when we arrived, and the aroma would have lured us in if the ambiance of this white clapboard inn hadn’t already. We stayed several days to enjoy catching up with our friends.

Then we caught the Down East Highway, where we passed the Coach Stop Inn, another historic place to stay. A multitude of antique stores and numerous cemeteries peppered the highway, attesting to centuries of buried ancestors.

Bennington, Vermont

We journeyed on to Bennington, VT, to see my partner’s ancestral home. Cheese, crackers and cookies greeted us when we reached the reasonably priced Eddington House. This inn (with narrow stairs, of course) features intriguing antiques and a hearty breakfast. The Old First Church has a graveyard with the burial site of Robert Frost and a soaring monument to the Green Mountain Boys, who fought in the Revolutionary War.

We crossed the covered Henry Bridge to discover that The Henry House, cherished in my beau’s family, is most deserving of its placement on the National Register of Historic Places. Its spread of acreage is trim, its riverbed full of trout, and the estate is meticulously maintained by owners who enthusiastically showed us the house and grounds. The house, built in 1769, is one of Vermont’s oldest surviving houses, and now hosts weddings and events.

As we departed via Highway 2 (The Mohawk Trail), multi-hued leaves floated down from their recent lodgings, bidding us farewell. I found myself singing John Denver’s “Annie’s Song:” “You fill up my senses like a night in a forest.” This drive through history awakened our senses with forests full of vibrant, wind-tossed leaves, the allure of the waterways and the aroma of those warm breakfast scones at the bed and breakfasts.