11 Prettiest Downtown Strips In Massachusetts
The past is more than a memory in Massachusetts. It is alive in the geometries of the architecture, in the poetry of the generational stories, and in the traditions that animate the culture.
Massachusetts is not simply an American state (or commonwealth, as locals will remind you) — in many ways, Massachusetts is America. It’s where the Mayflower found safe harbor in 1620. It’s where the American educational system took root 16 years later with the founding of Harvard. It’s the place where, as Emerson immortalized it, “embattled farmers stood, and fired the shot heard round the world,” igniting the American Revolution.
In small towns across Massachusetts, reminders of the past await around every corner and along every path. Given the colonial design of these towns, the best place to experience this cultural richness is at the very heart of each locality — the downtown. There you will find well-preserved streets that invite exploration and remembrance. Here are 11 downtowns that welcome each visitor on a pleasant journey of rediscovery.
Lexington
The Battle of Lexington and Paul Revere’s midnight warning of the British advance are foundational events in the American Revolution. This noble history is never far from the surface in downtown Lexington. Buckman Tavern, just off Massachusetts Avenue, is where minutemen gathered before the fateful encounter with British soldiers in April of 1775; the Lexington Battle Green is the actual battle site. The roots of the nearby First Parish Church are even deeper, reaching back to the 17th century. Popular resting stops include The Crafty Yankee gift shop and the Via Lago restaurant. Downtown offers a range of memorable activities, whether your preference is retracing the footsteps of John Hancock and Samuel Adams or hoisting a mug of Sam Adams at a local pub.
Concord
It’s hard to talk about the Revolutionary significance of Lexington without mentioning Concord, a smaller town seven miles to the west. The local militia fought off the British at North Bridge, a short walk from present-day downtown. Explore this proud history at the Concord Museum near Main Street. Literary connoisseurs won’t want to miss The Old Manse, a wooden Georgian-style Monument Street landmark that Ralph Waldo Emerson and Nathaniel Hawthorne called home at various times. This rich literary tradition lives on at Main Street’s Barrow Bookstore, featuring a trove of rare finds. Enjoy a newly purchased book with a cappuccino at the popular Main Streets Market & Cafe.
Salem
A darker history awaits in Salem, site of the infamous 17th-century witch trials. The town’s hub for mystery, excitement, and historical exploration is Essex Street, the central pedestrian mall. Salem’s tourist focus on its witchcraft hysteria past can be intense (on Essex, there’s even a statue of Elizabeth Montgomery, the actress who played Samantha Stephens on the classic "Bewitched" TV series), but there is much more to experience beyond such spellbinding attractions as The Witch House. Just off the strip is The House of the Seven Gables, a National Historic Landmark that inspired one of the great novels in the American literary canon. Art connoisseurs will want to make time to explore the Peabody Essex Museum. Finz Seafood on nearby Wharf Street is a popular spot to unwind and indulge in fresh-caught entrees while taking in the ocean views.
Northampton
Massachusetts is rich in premier educational institutions. Not since the time of Socrates, Plato, and Aristotle has there been such a concentration of teachers, students, and academic resources. Northampton’s Smith College is the epicenter of one such concentration, with Amherst College, Hampshire College, Mount Holyoke College, and the Amherst campus of the University of Massachusetts within a 12-mile radius. Downtown is a popular destination for students, who give Main Street its youthful, artsy, and often countercultural vibe. Visitors enjoy strolling past Victorian brick structures to intriguing destinations such as Thornes Marketplace, the home of independent retail shops ranging from Booklink Booksellers to Glimpse of Tibet. A centerpiece of the strip is the Academy of Music Theatre, a 19th-century venue where Mae West and Harry Houdini once performed and today features live theater, movies, and musical performances. Other popular stops include the First Churches of Northampton, a Gothic marvel nearly a century-and-a-half old, and the Northampton Brewery, located steps from Main Street on Brewster Court.
Provincetown
Provincetown is located at the tip of Cape Cod, bounded by the Atlantic Ocean and Provincetown Harbor, where the Pilgrims landed in 1620 and forged a cornerstone of American democracy, the Mayflower Compact. Downtown’s Commercial Street runs parallel to the harbor, providing incredible ocean views for visitors strolling past weathered facades, galleries, boutiques, and the occasional street performer. Try lobster from offshore traps at The Canteen. Sample the talent of resident artists at the Provincetown Art Association and Museum, or admire the Greek Revival architecture of the Provincetown Public Library. You can also pose at the Pilgrim Monument, not far off Commercial Street on High Pole Hill Road.
Sandwich
Sandwich is the place to experience Cape Cod’s oldest downtown with colonial charm unfurled along the cobblestone pathways of Main Street. The shore is more than a mile away, but downtown feels coastal, a salty breeze often rustling the strip’s ancient canopies. Main Street, lined with colorful cottages and white steeples, is an open-air museum for colonial architecture and design. The Hoxie House, just off Main Street on Water Street, is a wonderfully preserved saltbox home dating from 1675. The Town Hall is a Greek Revival structure built in 1834. The Dan’l Webster Inn & Spa offers authentic regional recipes, and Titcomb’s Bookshop, a few miles away, is the ideal place to search for rare finds. See craftsmen demonstrate glassblowing at the Sandwich Glass Museum for something different.
Nantucket
Thirty miles off the coast of Cape Cod is Nantucket, once one of the busiest whaling ports in the world. Today, it is sometimes referred to as “Billionaires’ Isle,” given the number of wealthy residents, a list that includes former Google CEO Eric Schmidt, and former New England Patriots coach Bill Belichick. Fortunately, Main Street’s cobbled streets, Greek Revival structures, and laid-back ambiance remain, accessible to tourists on modest budgets. Most visitors reach this island via ferry, which accounts for the low number of cars you’ll encounter. Start your downtown tour with a trip to the Nantucket Whaling Museum just off Main Street. Then explore Nantucket’s Quaker roots with a visit to Fair Street’s Friends Meeting House. Check out Nantucket Atheneum, a library and community gathering place that rose from the ashes in 1847, one year after a fire destroyed downtown. Complete your time travel adventure by transporting yourself to one of the island’s more recent fascinations, the world of preppy chic, by shopping at Murray’s Toggery Shop.
Rockport
Another great coastal downtown can be found in Rockport, a placid small town located on Cape Ann. The strip has a beautiful view of Sandy Bay with the Bearskin Neck section winding along the shoreline. Fishing boats bob in the near distance, supplying fresh crab, shrimp, and oysters daily, which original recipes turn into irresistible entrees at restaurants like the Roy Moore Lobster Company. The Rockport Art Association is the centerpiece of the art scene, showcasing local talent. The twin themes of fishing and art meet at Motif Number 1 on Bearskin Neck. The 19th-century red fishing shack has been so popular with generations of artists that it has been called the most often-painted building in America. Tuck’s Candy Factory off Main is the perfect sweet ending for your trip to Rockport.
Newburyport
Newburyport’s downtown stretches along State Street to Market Square, a riverfront plaza that is the site of musical performances, farmers’ markets, and soaring church spires. The Firehouse Center for the Arts is a cultural centerpiece. The First Religious Society on Pleasant Street, just off State Street, is a prime example of Federalist architectural design. The Custom House Maritime Museum on nearby Water Street is a great place to explore the town’s maritime history, which includes a vibrant shipbuilding industry in the 19th century. Back on State Street, sample Newburyport’s sea-caught bounty at The Paddle Inn.
Great Barrington
Great Barrington’s downtown represents both history and progress. Railroad Street is one of the oldest existing streets in the country. Main Street, by contrast, is known for a society-changing milestone: It was the first street in the United States to be illuminated by electric streetlights. The march of progress has further transformed downtown into a cultural hub brimming with theaters, cafes, craft breweries, small bookstores, and seasonal literary events. The Railroad Street Collective is a popular shopping destination, while The Prairie Whale restaurant attracts patrons looking for fresh, farm-to-fork meals. Admirers of great architecture visit the the Romanesque First Congregational Church building on Main.
Stockbridge
It’s no surprise that Stockbridge’s Main Street looks like something out of a Norman Rockwell painting. That’s because the quintessentially American artist lived in Stockbridge from 1953 to 1978. The town is proud to host the largest collection of Rockwell paintings in the world at the Norman Rockwell Museum, a short ride from Main Street. The downtown itself is a masterpiece of Americana beauty. The most authentic place to stay is The Red Lion Inn, built in 1773. For a special dining experience, visit Once Upon a Table, the popular restaurant that proudly lists on its menu the local farmers who grew each entree’s ingredients.
Time Passages
“Places remember what people forget,” author Richard Powers once wrote. The wisdom of that insight is on elegant display in the commercial heart of small towns like Lexington, Concord, Salem, Northampton, Provincetown, Sandwich, Nantucket, Rockport, Newburyport, Great Barrington, and Stockbridge. Remembrance is in the architecture, the landmarks, and the cultural celebrations. You’ll see it along cobblestone pathways, or hear its music in the leafy flutter of centuries-old maples. In these places, generations of historical drama, triumph, and achievement co-exist with the present in a tranquil and timeless panorama.
