10 Picture-Perfect Main Streets In Massachusetts
When you think of New England, you think of fall. You think of apples and pumpkins. You think of haunted holidays and festive light displays, beachside summers, or all-season hiking trips. Massachusetts is one of those states you think of, whether you know it or not. It is known for its autumn colors, magical air, deep-rooted colonial history, accents, and, of course, lobster. Travelling through the state, you can be sure that you will find amazing views, small towns, large cities, and eventually, a beach or two. However, if the goal is to find the most beautiful and picturesque main streets, then this list might make it a bit easier for you.
Falmouth
Falmouth is exactly what you think of when picturing a seaside main street. You can smell the ocean air. Feel the morning dew. And breathe the quiet start to a beautiful sunrise. However, it doesn’t last long in this main street area. The red-bricked sidewalks will be filled with walkers, bikers, and shoppers in no time. It's also a great place to simply take a stroll on a warm summer day. This long stretch makes you feel like you can see shops for miles, and yet it isn’t daunting or overwhelming. You can see beautiful views of Falmouth Harbor right there, putting it all in perspective.
Falmouth, which is made up of eight distinctive villages, is filled with character and charm. Main Street is lined with cozy bookstores, fashionable clothing boutiques, delicious bakeries, and several bars and restaurants. Kids will love the activities at Woods Hole Science Aquarium. There are lots of little shops where you can peruse nautical knick-knacks, jewelry, and local crafts. At the Falmouth Public Library lawn, feel the patriotic pride while looking at the statue of town native Katharine Lee Bates, who penned the patriotic anthem “America the Beautiful.” The town has live theater, harborside concerts, a jazz fest, and the acclaimed Woods Hole Film Festival each summer.
Edgartown
Edgartown, Massachusetts, is one of the most picture-perfect places in Massachusetts. As part of Martha’s Vineyard, it is an elevated way of life. There are beautiful beaches, the Mytoi Japanese Garden, and relaxation everywhere you turn. The best part is that Main Street isn’t very different. Edgartown Books is right in the heart and is an old-fashioned, independently owned bookstore. Grabbing a book or finding something quirky to enjoy while you sit on the bench on Main Street or at the beach is not an uncommon occurrence.
The hustle and bustle has a more relaxed feel to it. If you could slow time and just live for a few extra beats per minute, it would be here. Their beautification committee does such a great job. They have beautiful street lanterns and benches that add to the feeling of being in some romantic painting. In the winter, both are decorated with holiday lights to add to the festive storefront décor. When the snow falls, that frozen moment isn’t something to miss. There is plenty to do and see here as Edgartown hosts many annual events. However, the comings and goings for tourists and locals make Main Street a gathering point. It is no wonder their motto is “Discover your happy place today.”
Great Barrington
Great Barrington oozes appeal. It's a cozy, historic, brick town full of culture, music, art, and unique and trendy businesses, adding to the unique small-town flair. Wandering downtown, you’ll come across countless restaurants, bars, shops, galleries, and other attractions you look for on Main Street. Fun fact: the main street was the first American street to receive electric lights. Head over to Railroad Street for even more cool shops to explore. Tell everyone how you walked in history on one of the oldest streets in the United States that is still in existence. Don’t miss more opportunities to see what GB has to offer by taking a relaxing stroll along the public footpath of the Housatonic River as it winds its way through town and up to the village of Housatonic.
The beautiful tree-lined strip boasts locally owned and operated businesses. Stop by Fuel Coffee Shop, browse the eclectic and entertaining items in Tom's Toys, and when you're done on Main Street. Save your appetite for some of the vast creative food options. Get your steps by exploring the antique shops, art studios and galleries and boutique shops in the walkable half mile radius providing ample options, views and opportunities for Instagram photos.
Lee
Let’s start with the fact that you can sponsor a flower basket that hangs on the street lanterns in Lee. If that isn’t enough of a reason to note the Picture-Perfect appearance of Lee, then let’s get into all Lee has to offer. Lee’s Chamber of Commerce is over 100 years old, maintaining the goal to promote the town’s image and working with businesses to make it a destination not to be missed. From the Gateway Jazz Weekend to the Founders Weekend, the town is decorated according to the celebration. Taste of Lee offers a celebration for the restaurants and encourages people to give the local restaurants some well-deserved shine.
Main Street is the “shopping capital of the Berkshires”. A wide array of shops, from premium to eclectic, you’ll find what you are looking for, and more! Lee is loaded with cool shops, great dining spots, and places to watch the crowd roll by. Try the Starving Artist Creperie and Cafe for a sweet snack or head to Moe's Tavern to wrap up shopping with a drink. Tables and patios are available at a few of the restaurants, and the car-lined streets don’t even dampen the beauty of the street. The walkway is clear, and at night, when the lights come on, the ambiance turns even more breathtaking. You will sureLEE love it here.
Rockport
When you walk through the holiday decorations with the painted winter scenes, you think, “That is a place to spend the holidays.” That is Rockport. Rockport is a cute and historic town out of a fairytale. To say it is charming would be an understatement. Rockport mixes small town with seaside in what can only be described as the most picture-perfect and romantic town. The views are amazing, both beautiful and terrifyingly striking, despite the weather. Not that it should be a surprise, as the town’s boulder-strewn paths through woods and glades, and that uncommonly magical light that has inspired painters since Winslow Homer.
The downtown area is located on Main Street and Bearskin Neck, but the area is jam-packed with art, galleries, shops, and photo-ops worth the use of your storage. It's not only an artist friendly community but inspiration is around every bend, so it is encouraged. There is no shortage of sculpture, painting, or picturesque spots. Spirited enthusiasm doesn’t stop there; the town decks out for the Harvest Fest by the sea and a rocking Christmas in Rockport, over a month-long festival that almost everyone downtown takes part in. The street might not be brick, but your trip down Main Street will surely rock!
Stockbridge
Stockbridge is often referred to as the spirit of a Norman Rockwell painting, but it goes much further than that. You can actually buy Norman Rockwell memorabilia, as he spent the last 25 years of his life there. The Norman Rockwell Museum emphasizes the connection between the two. The Naumkeag botanical gardens can also inspire you. Knowing this, one can only assume that Main Street is something remarkable to be an inspiration to such a talent. It is. Browse the shops, stop by the historic Red Lion Inn, and grab a tasty meal at Once Upon A Table.
Well known for its Main Street at Christmas, Stockbridge is a transformative place. Twinkling lights and holiday décor don’t just encourage the holiday spirit; they demand it. The already enchanting destination only captivates more in the holiday season with live performances, holiday markets, and spellbinding light displays. Rockwell’s painting comes to life and roams the streets. The ordeal is so grand that it has its own articles and links on its website. The shops on Main Street work outside the season to show festive spirit for holidays all year round. Showcasing a themed Jack-o-lantern in the fall, or a sidewalk display for the arts festival, Stockbridge is stocked with Picture-Perfect moments on Main Street.
North Adams
North Adams is a hot spot getaway for a bustling Main Street. This town calls for the quirky, the artists, the DIYers, and the outdoor enthusiasts to reflect the community’s way of life. Festivals and events are held throughout the year, drawing people to explore and enjoy all this town has to offer. Visit the Farmers March, Fresh Grass Festival, Winterfest, Easter Fest, Pridefest, Fall Foliage parade, haunted house, tree lighting, and more. All pulling people downtown. The Downtown Celebration has tents popping up and down Main Street so visitors and locals alike can join together and find something they didn’t know they needed. The main street packs a ton of stuff to do into a relatively small space.
Stop by Jack's Hot Dog Stand for a delicious bite to eat, peer into the quirky ships, or watch a show at the Mohawk. Then head to Mass MoCA for a fun dose of culture and art. MASS MoCA doubled in size in 2017, and it’s considered the largest contemporary art museum in the United States. The light exhibitions by James Turrell at MASS MoCA are worth a thousand words. Lively, trendy, and just fun, you won’t even need to say cheese.
Concord
The level of fame and history in Concord runs deep. History buffs will find a lot to nerd out on, like the first shots of the Revolutionary War were fired here. However, bookworms can find ties to several cherished American literary works, all of whom once lived and were inspired by Concord at one point. The Old Manse, where poet Ralph Waldo Emerson drafted his essay “Nature” in 1800, and Walden Pond, made famous by writer Henry David Thoreau, are both located in Concord. You can even visit Little Women author, Louisa May Alcott’s Orchard House.
Concord is undeniably one of the prettiest small towns in New England. This historic community also happens to have an incredibly picture-perfect main street. Concord’s town center is home to many restaurants on the town’s Main Street, including Helen’s, Haute Coffee, and Sally Ann's Bakery and Food Shop. Shop the many eclectic and unique shops like A New Leaf, Artisans Way, and Revolutionary Concord. Concord Bookstore has works by local authors.
Newburyport
Newburyport may be a seaside must-see, but it also has a deep history that dates back to before the Revolutionary War. Originally, the area was inhabited by the Pawtucket Indians. Its popularity started rising around abolishment of slavery when it became an important stopping point on the Underground Railroad. The town grew from there, adding factories, docks, and whaling fleets. It is home to the Topsfield Fair, America’s Oldest County Fair, which began in 1818. Its growth doesn’t end there. The more it grew, the more its Main Street shaped.
Today, Newburyport boasts a mix of modern and old-fashioned enjoyments. Whale watching tours and the Custom House Maritime Museum speak to its maritime roots. Walking the Main Street showcasing Federal-style brick buildings and museums, Market Square is listed on the National Register of Historic Places. Walk the downtown streets and enjoy the beauty that comes in the form of charming flower boxes that decorate storefronts, as well as the unique coastal must-haves displayed within. The shop owners strive to exceed expectations. You’ll also find a slew of antique shops, including Oldies Marketplace, The Cottage, and Green Plum Vintage Goods. Enjoy the natural beauty of the Newburyport Waterfront while you shop, eat, and make picture-perfect memories.
Salem
The most picture-perfect Main Street in Massachusetts is none other than Salem, Massachusetts. Home to one of the arguably most terrifying historical events, with answers people can only speculate about, Salem doesn’t shy from their past but embraces it. You can visit the Salem Witch Trials Memorial and the Salem Witch Museum. Visit the Witches' House or take the “History and Hauntings of Salem" tour by Witch City Walking Tours. Also capturing some spotlight is their Maritime roots, traveling to Salem a thrilling, and educational opportunity. If you want to explore outside the folklore and haunting rumors of Salem, stop and enjoy the Peabody Essex Museum, the oldest continually operating museum in the United States. There is plenty to do or try.
However, the real winning part of Salem is Essex Street. This cobblestone road is in the heart of Salem. It only allows foot traffic on the road for its pedestrian mall. The cobblestone walk is a rare feature to see and adds to the ambiance of shopping in this unique space. Looking down the street is amazing, and you see tourists constantly taking pictures to marvel at for years. Travelling down the street is lined with boutiques, souvenir shops, restaurants, cafes, and adorable streetlamps. The names of the businesses even add to the magic of this Main Street. Essex Street in Salem is sure to put a spell on you.
You can’t go wrong exploring Massachusetts. So many more places exist within the state and the atmosphere, and size encompasses the entire spectrum. Picture-perfect moments, places, and things can be sought after or pop up on a whim. You could travel the state and find beauty everywhere. A lot of us long to see those Main Streets from the movies and TV shows. The towns where just existing are peaceful, and magic and beauty are in abundance. Connection and community, and everything you need, all lined up, and the shopkeepers remember your name. We might not find that on a spur-of-the-moment trip, but with the list above, we can get pretty close. Experience those picture-perfect Main Streets and experience life differently.
