A New England Road Trip From New York To Maine

New England Road Trip: Portland, Maine skylineiN

My colleague and friend, Lori Tripoli*, took a slow New England road trip to relax and unwind but says for the time-crunched, the same itinerary can be speeded up over a long weekend. She suggests a leisurely two-night stay in each city along the way to enjoy the shops, dining and water views. 

Leaves or no leaves, a late fall or early winter New England road trip proves the perfect escape for a “new” way of travel.

Pre-pandemic, the focus of our trip would have been on seeing as many sights, visiting as many shops, and hitting as many hot restaurants as we possibly could. In these socially distanced times, what we really crave is a getaway where we will feel safe. In search of lodging that offers comfort and refuge and in-house dining, we hit the road heading to Maine.

Our New York to Maine Road Trip Itinerary

A lighthouse in Maine
A lighthouse in Maine (credit: G Johansen Pixabay)

Maine—known for its hardy, salt-of-the-earth populace and lobster rolls worth traveling for—that is just over four hours by car from New York’s Westchester County, becomes our first destination. As much as we do not, right now, want to fly anywhere, we are also wary of spending too much time on our New England road trip in the car. We opt to undertake the longest leg of our journey on Day 1 with a plan to meander back to home base slowly.

Portland, Maine serves as a strategic as well as a charming first stop. Disinclined during these germ-conscious times to patronize rest stops or service station restrooms, I will just about have reached my limit around the time we are pulling up to the valet parking at the Portland Harbor Hotel.

Arriving in Portland, Maine: Where to stay and what to do

Contemporary guest room at the Portland Harbor Hotel (courtesy Portland Harbor Hotel)
Contemporary guest room at the Portland Harbor Hotel (courtesy Portland Harbor Hotel)

Located in the charming Old Port District just a block from the waterfront, the Portland Harbor Hotel, a 101-room boutique, oozes with nautical charm and comfort. After a speedy and friendly check-in, we freshen up in our room before heading out to explore the waterfront and indulge in a little window shopping. There will be time for a long soak in the tub with a book in hand later.

We’ve barely reached Portland Harbor when we realize it’s the right choice for an off-season vacation during a pandemic. With a population of about 1.3 million people in the entire state, Maine proves a wise and uncrowded option. As we amble toward the harbor, we notice that Portland, a small city with just 68,000 inhabitants, features plenty of open and walkable space. More importantly, the people we encounter are friendly. We’ve left New York’s brashness and cynicism behind.

If you’re not watching boats come in and out, indulge in some recreational shopping at Lisa-Marie’s Made in Maine if you are interested in locally made items (including sea glass bracelets!). FatFace is a good choice for those in search of clothing for anyone in the family, and Sea Bags offers unique handbags made from old sails.

Evening city view from the hotel (credit: M. Ciavardini)
Evening city view from the hotel (credit: M. Ciavardini)

Ready for a rest and maybe a movie in the cozy living area of our accommodations, we head back to the hotel. Interested in Maine’s history­­—and its prior existence as part of the Commonwealth of Massachusetts—I reread Laurel Thatcher Ulrich’s A Midwife’s Tale, the annotated journal of a midwife who lived in the 1700s.

Autumnal dining at the Blue Fin Restaurant

Recharged a few hours later, we head to the Blue Fin restaurant for dinner. Being, as we are, at the height of the pumpkin spice season, a Pumpkin Pie Martini seems the perfect choice to kick off an evening now.  

In years past, hotel restaurants would rarely register in my awareness; if anything, they’d be a convenient afterthought, a place we might slip into for a late-night cocktail or a convenient morning breakfast. Now, however, they factor hugely in my planning as we try, as much as possible, to dine in situ. It’s part of our new travel cocooning where, despite forays into the real world, we like to retreat to a cozy refuge, one where we won’t feel like hundreds of strangers and all of their germs are hovering.

We revel when, not long into our salad course, a small team from a nearby business arrives for a social gathering celebrating something corporate. For us, as visitors, an imprimatur of a restaurant’s legitimacy is when locals frequent a place. Even more enthused by the positive energy of our fellow diners, we fill up on surf and turf before settling in for a long evening’s nap.

The possibilities of things to do in Portland, Maine, are endless.

Next Stop: A Quiet Stay in Boston

New England Road trip: A room with a view at the Boston Harbor Hotel
A room with a view at the Boston Harbor Hotel (credit: M. Ciavardini)

Emboldened by the success of our visit to Portland, we drive south two hours to Boston, where, continuing our indulgence in sequestered destinations, we plan to hole up in a suite in the Boston Harbor Hotel.

One of the few positive developments in travel associated with the pandemic is the emphasis on speedy and painless check-in. As in Maine, the process is quick. It seems to take just seconds before a bellman is whisking us to our room and giving us a quick lesson on how to operate the bedside tablet from which we can not only control the ambiance but also order room service.

Room service at the Boston Harbor Hotel
Room service at the Boston Harbor Hotel (credit: M. Ciavardini)

Again focusing on relaxing—reading, soaking, staring out at the view—we spend quality time in our room that in the “before” times would merely have served as a sleeping place in-between visits to local sites. Now, we only venture downstairs for dinner and more water viewing.

We indulge in espresso martinis and a seafood tower at Rowes Wharf Sea Grille in the hotel. Indulging in some socially distanced people-watching—tables are situated at a comfortable distance from one another—we simultaneously enjoy more harbor views.

Those more motivated than we are might enjoy a visit to the Museum of Fine Arts for some good art, an informative walk on the Freedom Trail for a dose of Revolutionary history, and a stop-in at the Brattle Book Shop (established in 1825!) for more reading material.

On to Concord, Massachusetts

Louisa May Alcott grave in Concord (credit: M. Ciavardini)
Louisa May Alcott grave in Concord (credit: M. Ciavardini)

On a prior visit to the land of Louisa May Alcott (she and her family lived in Concord and visitors to the Orchard House can see where she wrote Little Women in just a few months), I discovered Concord’s Colonial Inn, a historic inn that dates to 1716.  We stop by for a restful lunch at Liberty where we order some classics: Waldorf Salad (a concoction of apples, grapes, greens, and tarragon dressing), a lobster roll, and Yankee pot roast. Afterward, I head to The Concord Bookshop, a charming independent bookstore, for more nourishment for my reading addiction.

As is our habit, we swing by Authors Ridge at Concord’s Sleepy Hollow Cemetery before heading to the next stop on this very different New England road trip. The ridge is the final resting place of Louisa May Alcott, Nathaniel Hawthorne, Henry David Thoreau, and Ralph Waldo Emerson. I keep lingering on Alcott’s speed—she was an impressive producer of content who churned those words out without the benefit of a laptop. Maybe leaving a pencil or two at her grave as sacrifices will help me overcome my own shortcomings as a writer.

If you’d like to linger, book a stay at the inn itself and consider that Alcott house tour.

Last stop on our road trip: Newport, Rhode Island

Guestrooms at Bannisters Wharf in Newport, Rhode Island
Guestrooms at Bannisters Wharf in Newport, Rhode Island

A swing by Bannister’s Wharf in any season may seem counterintuitive during these socially distanced times. Being, as it is, at the heart of all that is Newport, RI, the destination does tend to draw a crowd and plenty of sailing sorts. On this New England road trip, we plan to stay above the fray—and away from the vapors—by booking a room in the Bannister’s Wharf Guestrooms overlooking the marina in Newport Harbor.

The luxury here is the million-dollar view and the second-floor deck that is open only to guests who’ve booked a room. Yes, a stay here ever so slightly is akin to staying in someone’s fishing shack. But this is Newport and, without ever descending to sea level, you can watch the yachts dock, the sunrise and set, and smaller vessels head out to open water.

View from our guest room at Bannisters Wharf
View from our guest room at Bannisters Wharf mat (credit: M. Ciavardini)

We do actually have to venture downstairs to dine. Foodies will enjoy comparing the products of 22 Bowen’s Wine Bar & Grille (modern and sleek) and the Clarke Cooke House (more animated and earthy). You’ll want reservations for each.

If you’re in the mood for fancy—in terms of food or accommodation—head to The Chanler at Cliff Walk, one of the mansions (quaintly referred to as ‘cottages’) on Newport’s famous Cliff Walk. Reservations for the cafe at The Chanler are a must.

Elegant dining room at Chanler at Cliff Walk
Elegant dining room at Chanler at Cliff Walk (credit: M Ciavardini)

Ever wonder what it would be like to take a road trip around Maine in an RV? Read about this coastal Maine road trip

*About Lori Tripoli

Lori Tripoli is an accomplished freelance writer and editor focusing on law and the legal business, environmental policy and sustainability, higher education and travel. Lori was a founding editor of Sustainability: The Journal of Record and was editor of the New York Law Journal Westchester Edition.

A city kid by inclination, she has, in more recent years, embraced adventures in rain forests and caves. Lori’s passions are environmental conservation, travel and writing personal and professional histories. She blogs about her globetrotting habit as the Bashful Adventurer.

Disclosure: The author’s visit to the Portland Harbor Hotel was sponsored by Colwen Hotels, which manages the hotel.

IF YOU GO           


Note: The distance from Bedford, NY to Portland, Maine is about 279 miles. The Google map shows the round-trip distance/driving time.

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