This Massachusetts Downtown Is Made For Strolling
With just under 20,000 residents, Newburyport, Massachusetts, about 45 minutes north of Boston, invites easy wandering. Its compact downtown is dotted with cafés, shops, and galleries just minutes apart, while narrow, brick-lined streets create a welcoming, human-scale atmosphere. The area feels lively without being crowded, encouraging a slower pace and letting you take in the architectural details and historic charm.
Market Square, State Street, and the Merrimack River waterfront anchor the downtown core. Brown Square, home to the Garrison Inn and local memorials, sits just beyond, followed by Water Street, where the Custom House Maritime Museum highlights the town's maritime past. These landmarks and the streets connecting them reveal Newburyport’s character block by block. So come along and enjoy a stroll through Newburyport's charming and walkable downtown!
Market Square
Market Square has long served as the commercial center of Newburyport. During the 18th century, it was a gathering place for merchants and traders tied to the river-based shipping economy. Its location at the intersection of several major roads, rather than as a formal square, still defines the area today.
After the Great Fire of 1811, much of downtown was rebuilt in brick. The three- and four-story commercial buildings that surround Market Square reflect early 19th-century urban design, with ground-floor businesses and upper-level offices or residences. Today, Market Square connects seamlessly to surrounding streets, the waterfront, retail areas, and dining spots, keeping the square at the heart of downtown life. Check out the historic 1823 Market House to ground yourself in this town's history.
State Street
From Market Square, head toward State Street, one of Newburyport’s liveliest downtown stretches. Begin your stroll at LEALLO, a boutique offering curated home goods, décor, and lifestyle items. Seasonal displays in the window invite you to browse without breaking the flow of your walk. A few doors down, Brine serves oysters, salmon crudo with citrus and arugula, lamb croquettes, and bone-in prime ribeye, making it a standout stop for seafood or a hearty meal.
Nearby, the Stonewall Kitchen: Newburyport Company Store offers locally made sauces, jams, and condiments with tasting stations and gift-ready packaging. Across the street, Anchor Stone Deck Pizza features a rustic interior and open kitchen where wood-fired pizzas like the Pesto Caprese and Newburyportabella are prepared in view. For a mid-walk pause, The Coffee Factory serves drinks made with locally roasted beans. Artwork lines the walls, giving you something to admire while waiting for an espresso or latte, and fresh pastries are available to enjoy alongside your coffee.
Merrimac Street's Waterfront Park
From State Street, take a 10-minute walk to Merrimac Street, which runs parallel to the Merrimack River. Shops and restaurants gradually give way to open space and river views, leading to Waterfront Park. The 4.4-acre park, managed by the Newburyport Waterfront Trust, features a sculpture garden, grassy riverfront areas, memorial benches, and a 1,100-foot boardwalk perfect for photos or watching boats drift by.
The park also hosts outdoor exercise classes, summer weddings, and performances ranging from local theater to world-class concerts during Yankee Homecoming and the Riverfront Music Festival. From the boardwalk and park paths, you can enjoy panoramic views of anchored yachts, passing vessels, the opposite shoreline, and bustling downtown docks. After enjoying the waterfront, loop back toward Market Square via Inn Street.
Inn Street & Pleasant Street
On Inn Street, Simply Sweet offers handmade candies like sea salt caramels and chocolate turtles, along with one of the area’s largest selections of chocolate barks and over 40 ice cream flavors, served in a cup or hand-dipped waffle cone. A few doors down, Jefferson Road features thoughtfully selected women’s clothing and accessories. Nearby, the Inn Street Fountain & Splash Pad provides a small area with water jets and benches, perfect for a quick rest or watching families at play before continuing your stroll.
At the end of Inn Street, Pleasant Street has several eateries, including Oregano Pizzeria & Ristorante, serving brick-oven pizzas, Mediterranean small plates, grilled lamb kabobs, pasta, and salads, with outdoor seating in warmer months. Nearby, Loretta blends classic American and seafood-forward dishes with seasonal flair. On Sundays, live jazz adds a lively touch to the dining experience.
Additional Stops: Brown Square & Water Street
From Pleasant Street, take a short walk to Green Street, which leads to Brown Square, home to historic buildings including the Garrison Inn. Originally opened as the Brown Square House in the early 19th century, the property was associated with prominent local merchant Moses Brown and later became the Brown Square Hotel in the late 1800s. By 1923, it was rebranded as the Garrison Inn, honoring abolitionist William Lloyd Garrison, whose statue stands in the square alongside several veteran memorials.
From Brown Square, continue along Green Street to Merrimac Street, then follow it to Water Street to visit the Custom House Maritime Museum, which has exhibits on shipbuilding, trade, and seafaring life, as well as rotating events that celebrate Newburyport’s connection to the river.
Other Downtown Areas In Massachusetts
Beyond Newburyport, other Massachusetts towns also offer walkable, historic downtowns. Stockbridge, about a three-hour drive west-southwest in the heart of the Berkshire Hills, features a charming Main Street with the Red Lion Inn and the Historic New England Merwin House nestled among mature trees and classic New England architecture.
Marblehead, just under an hour southeast of Newburyport, is equally worth exploring. Its Old Town downtown has narrow streets like Washington Street and State Street, where cafés such as Mookie’s at Mugford, galleries like Arnould Gallery & Framery, and seafood spots like Maddie’s Sail Loft sit within easy walking distance. A 20-minute stroll from the center leads to Fort Beach, Fort Sewall, and scenic views of Marblehead Harbor, adding a historic and coastal dimension to the downtown experience.
Strolling Through The Heart Of Town
In Newburyport, everything unfolds at a comfortable, walkable pace. You can move easily from shops and cafés to river views and quiet squares without thinking about distance or directions. A coffee stop turns into a lingering stroll, a simple outing becomes time spent by the waterfront, and well-traveled paths reveal hidden details waiting to be discovered. The downtown’s scale encourages you to slow down and explore naturally, letting the day unfold on its own. More than a collection of streets and landmarks, Newburyport offers a downtown where walking allows you to connect with the town’s rhythm, character, and everyday life.
