Lifelong residents on must-do city activities for Boston visitors

"Boston is one of the great American walking cities."

Pedestrians on the Boston Harborwalk. Wendy Maeda / The Boston Globe

Boston visitors have endless options for how to fill their time in this historic city full of museums, parks, restaurants, and quaint neighborhoods. So where should newcomers go?

We asked 15 lifelong Massachusetts residents for must-see Boston attractions and the following enthusiastic responses should help fill in any itinerary gaps. Here’s what they had to say.

Joe Fallon, concierge at Fairmont Copley Plaza and a resident of Marshfield:

“For a quintessential Boston experience, I recommend a stroll on the Boston Harborwalk to take in the beauty of our waterfront and capture plenty of photos. Then head to the North End for a classic Italian feast (you can’t go wrong with any of the restaurants) followed by dessert and cappuccinos at the quaint Caffè Paradiso.


Clarrissa Cropper Egerton, co-owner of Frugal Bookstore and a resident of Dorchester:

“New visitors should experience the National Center Of Afro-American Artists in Roxbury, also known as the ‘Big Head Museum.’  The magnitude of the grand metal sculpture in a sea of green grass is stunning, inviting, and a staple in the neighborhood. The center hosts events to highlight and bring awareness to the community as well as the history of the collected artwork of Black artists in the area.”

Billy Senné, president and CEO of Senné and a resident of Cambridge:

“For Boston visitors, and even lifetime residents like myself, taking a tour of Fenway Park is something everyone should experience, even if you are not a baseball fan. No matter how many times I’ve been to Fenway for Red Sox games, it never fails to impress, and you’ll learn something new about America’s oldest ballpark.”

Will Gilson, chef/owner of Puritan & Company and The Lexington and a resident of Acton:

“Stroll along the Greenway where you can start in the North End by the Carousel and take in the fountains, art installations, and beer gardens. Follow it until the end in Chinatown and stop at some of the independently owned restaurants along the way.”


Paul McCaffrey, director, permitting division at Boston Parks & Recreation Department and a resident of West Roxbury:

“Walk the Riverway in mid-October. The vibrant color of the trees and quiet in the middle of Boston is soothing.”

Nikia Londry, CEO of Intriguing Hair and a resident of Hyde Park:

“Visitors should visit Empire restaurant at the Seaport. Great food, drinks, and ambiance.”

Tony Dinatale, director of engineering at Four Seasons Hotel One Dalton Street, Boston and a resident of Melrose:

“If you come to Boston, you must go see Paul Revere’s house in Old North Square in the North End. Almost 250 years ago our American history started right here in Boston at that house. You have the luxury of being able to walk the entire Freedom Trail and relive his famous ride and if you don’t have time to walk the entire Freedom trail — the house is definitely a must-see. Take advantage of being in the heart of the North End and walk around the corner for gelato and people watching at Caffè Dello Sport — it just doesn’t get any better.”

A Swan Boat operates in Boston Public Garden in June 2016. – Jim Tuttle

Gary Saunders, chairman of Saunders Hotel Group, and a resident of Brookline:


“Take a stroll around the Public Garden to see the iconic ducklings, Swan Boats, and the Back Bay’s beauty all in one location!”

Jason Santos, chef/owner of Buttermilk & Bourbon, B & B Fish, and Citrus & Salt, and a resident of Woburn:

“Visit the Chinatown neighborhood of Boston on a Sunday afternoon for Dim Sum. My favorite spots include China Pearl, Hei La Moon, and Gourmet Dumpling House. Be sure to bring an empty stomach and then when you are done, walk it off around Beech Streets and Tyler Streets to take in the energy and excitement.”

Ed Kane, owner of Big Night and a resident of Boston:

“Bring a comfortable pair of walking shoes and start walking.  Whether is a stroll up Newbury Street and the Back Bay, or along the Charles River and Beacon Hill,  the Public Garden, the Freedom Trail, the North End, and the entire waterfront right down to the Seaport, Boston is one of the great American walking cities.”

Lydia Shire, chef/owner of Scampo and a resident of Stoneham:

“Wander Beacon Hill and end up at the Arlington Street Church to see the world’s largest collection of Louis Comfort Tiffany’s windows in a church… 16 in all, then off for a lobster roll in Faneuil Hall.”

Cathy Zemaitis, director of development at NEADS World Class Service Dogs, and a resident of Westborough:

“I can highly recommend a Boston Duck Tour to any first-time Boston visitor…I can even recommend a Duck Tour to anyone who has ‘been there, done that.’ If you think you know all there is to know about Boston and her long and illustrious history, think again. Jump on board a Duck and be entertained, educated, and enthralled by any one of the tour guides.”


Leah Tynan, employee at the Museum of Science and a resident of Cambridge:

Head to Lynch Family Skatepark. “The park is large (despite being hidden away!), has a lot of variety, and great energy. It attracts people of all ages and skill levels. The setting is awesome, with the Boston skyline visible from some angles and beautiful North Point park surrounding it.”

Caitlin Doyle, manager of community arts operations at the Museum of Fine Arts, Boston and a resident of Bridgewater:

“Take the ferry to visit the Boston Harbor Islands to swim, have a picnic, or camp. You’re so close to the city, but feel like you’re a world away.”

Renée Moran, physician and owner of Dr. Renée Moran Medical Aesthetics, and a resident of Chestnut Hill:

“Have a beer and a cup of chowder at the oldest bar and restaurant in the country at Union Oyster House and Bell in Hand Tavern and then walk along the Freedom Trail.”

17 must-do Boston activities, according to readers:

Responses lightly edited for clarity.


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