Walk The Walk: A Guide To New England’s Most Walkable Downtowns

You’re supposed to be at your most carefree while vacationing — so why worry about pursuing parking spots or dodging traffic? With historic sights and acclaimed attractions around every corner, New England’s vibrant downtowns were meant to be explored door-to-door. Shelve the car keys and take the first step in planning your walkabout with our guide to walkable New England cities.

                                                      Explore other Fall Offers

Most Walkable Cities in New England

This Street Is Made For Walking: Burlington, Vt.

Church Street, the heart and soul of Burlington, has one simple rule: walking only. This charming boulevard of brick functions like an outdoor mall, with specialty stores, coffee shops, restaurants, and even a town shopping center lining its four blocks. Summertime on Church Street sees the return of lively street performers from musicians to acrobats, while those invigorating winter evenings are illuminated by the swoon-worthy sight of twinkle lights and a 40-foot Christmas tree. While every visit aims to please, keep a close eye on the Church Street events calendar — spirited parades and festivals can keep the Burlington experience fresh for a lifetime.

Historic And Convenient: Portland, M.E.

Aside from succulent Maine lobster and awe-inspiring lighthouses, walkability is a huge hallmark of Portland. Bus stations abound, making this downtown journey as simple as picking a neighborhood, hopping on a bus, and embarking on your walking tour of Portland’s historic architecture. If you’re unfamiliar with The Forest City, learn the in’s and out’s on a seasonal guided tour with Greater Portland Landmarks, or fly solo for a self-guided walking tour. Some of the most stroll-worthy spots include the Old Port Historic District for its colonial maritime heritage, or the Victorian neighborhood of Western Promenade whose 19th and 20th century structures and gardens are like a travel back in time.

A Nearby Taste Of Maine: Ogunquit, M.E.

Many of Ogunquit’s hotels are nestled right near the area’s finest shops and restaurants, so scouting out a new seafood spot is as easy as taking a new turn off Main Street. From there, you can meander down The Marginal Way (a scenic walking path of breathtaking ocean views) all the way to Perkins Cove — where you’ll find another group of acclaimed restaurants by the sea. If you want to give your legs a break, hop aboard one of Ogunquit’s classic trolleys that run from Perkins Cove and all the way up Route One.

A City Meant For Moseying: Boston, Mass.

It should be no surprise that Boston found its way onto our list of walkable destinations in New England. Its public transit system and compact nature negates the need for a car, giving it the affectionate nickname of “America’s Walking City”. Head to the Downtown Crossing area to eat and shop some of Beantown’s best, see a show at a local theatre, and walk along waterfronts and flowerbeds at the Boston Common. On a nice day, take your steps back to the start of the American Revolution and follow The Freedom Trail along a 2.5 mile route complete with 16 historical sites.

A Stroll By The Sea: Newport, R.I.

Ocean lovers, we know how easy it is to lose yourself during a seaside stroll — that’s why you may need to keep your map open as you walk downtown Newport. The most popular downtown districts for dining and shopping, Bowen’s Wharf and the 5th Ward are both located along the seafaring Thames Street. Reveling in glistening ocean views are part of the experience during a door-to-door walking tour as well as a ride on the historic Newport trolley. Before you lace up your walking shoes, park your ride at a New England inn or resort that keeps you close to a downtown fit to fill an on-foot itinerary. We’re here to help you tour the best and brightest walks of New England — at your own pace, of course!