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Small Town Living in Massachusetts

In this world of overdevelopment, there are still Bay State communities that have not changed much through the years -- these are classic towns to live in, or, in some cases, as part of your New England vacation plans!

Shelburne Falls, Massachusetts

Shelburne Falls, Mass.

by Eric Hurwitz. Article updated on 11/20/16

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Many Massachusetts communities that we think of as classic small towns have become supersized. Due to growing tourism and other types of community development towns like Plymouth and Salem -- while essential New England travel destinations -- are no longer quiet, small towns. Still, Massachusetts does have some towns stuck in time, thankfully having no ambition to become other than what they always have been.  They are relatively undeveloped towns in comparison to other communities in the region. While the storefront names might have changed and there might be some more boutiques and galleries than before, the small town feel strongly remains in the following New England towns, filled with peace and quiet:

Boston Suburbs

Wrentham does have the gargantuan Wrentham Shopping Outlets on the outskirts of town, but the rest of this classic New England community is quintessential New England with a beautiful downtown featuring a handful of shops and restaurants (inlcuding the very good Gavel House)), a large, tree-shaded town common, church with tall white steeple, and public schools schools -- a typical, traditional combination for a New England town .  Lake Pearl and Lake Archer are true jewels, making Wrentham feeling like a vacation destination. The Big Apple Farm, in the quaint Sheldonville section of Wrentham, is a pleasant place to buy produce, pick seasonal fruit and enjoy a Richardson's ice cream at the ice cream stand. Sheldonville, by the way, is a sight to behold, consisting of a post office, general store and lots of scenic open spaces and farms off the main road (Route 1A). It's hard to believe Wrentham is a Boston suburb, given its Vermont village feel and the beautiful rural drives that seem so rare in in the suburbs.

Right next to Wrentham is Norfolk, one of the last truly  unspoiled small towns in the Boston suburbs. The town center, while still a work in progress (it's not finished yet, amazing for a town first incorporated in 1870!), has a beautiful town common with a gazebo, old-fashioned clock, a new library that fits in well with the "old" look of the town, a big white church, well-maintained colonial homes, and nice town common sidewalks to stroll. Norfolk also has Jane and Paul's Farm, a nice hideaway where you can buy some of its fresh produce and enjoy communing with the goats, chickens, rabbits and ducks.  It's a great place to go apple and pumpkin picking in the fall, and strawberry and blueberry picking in the summer. Norfolk also features numerous ponds and lakes. Mass Audubon's Stony Brook Reservation features an extensive boardwalk system to allow you to view a row of beech trees at Kingfisher Pond and turtles, muskrats, great blue herons, various duck species and more. It's a beautiful rural hike, seemingly located in the middle of nowhere. Norfolk is a true, community-oriented town with a friendly feel and also a skating rink where three generations of local family teach locals how to skate.  There's also "restaurant row" on Route 1A -- the Horse and Carriage for straightforward but excellent chicken, steak , seafood and pizza dishes, Novato's for traditional and modern American cuisine, and the Eagle Brook Saloon with its western bar/restaurant look, curved staircase and some of the best steaks around. Overall, Norfolk might seem unerwhelming, but it's overwhelmingly beautiful for those in search of small town New England.  Here's some more validation of Norfolk's small town feel: they still have an independently-owned weekly newspaper called the Boomerang, and no major highways touch this quaint town!

Concord still retains a small town feel, which is unusual for a town that could have gone "touristy" given its Revolutionary War history.  The lovely Monument Square, the quaint 1792 Colonial Inn hotel and restaurant, a few blocks of upscale yet low profile shops, the charming Concord Public Library built in 1873, and nearby famous Walden Pond (great for swimming and hiking) and the visually beautiful historic Old North Bridge area make Concord a relaxing vacation choice for those who don't want to be too overwhelmed during their travels. 

Neighboring Maynard is a hiddden gem. While it is not exactly refined and is still rebounding from the closing of Digital Corporation, you'll find a sunny downtown area and tree-lined neighborhoods with modest homes that seems stuck in the 50s.  The downtown features a growing restaurant scene, offering many types of ethnic food. Some of our favorite Maynard memories: the old school style China Ruby Chinese restaurant, the "It's a Wonderful Life" look of the Maynard Outdoor Store, and the last of a dying breed, Fine Arts Theater, that recalls the days of going to the local downtown movie theater.  There's also Babico's for diner comfort food and delicious donuts. On the outside of town is Erickson's, a classic ice cream stand has brought in summer crowds since 1937.

Manchester-by-the Sea is a wealthy North Shore town, just 20 miles north of Boston.  With a beautiful harbor, the cozy Singing Beach on the ocean, historic sea captains homes and buildings, and a modest but pleasant choice of downtown restaurants and shops, Manchester-by-the-Sea really turns on the coastal New England charm to the highest degree possible. It is also close to Rockport and Gloucester, two renowned New England coastal vacation destinations.

Southeastern Massachusetts

Marion, a charming residential seacoast community, offers a general store, neighborhoods with well-maintained large homes with white picket fences, and water views along Buzzards Bay near Cape Cod.  Marion is home to Tabor Academy, a renowned private school.

Middleboro, near Cape Cod, has a spectacular 1870s Victorian-style town hall that is rumored to be haunted, an old-fashioned downtown with a nice mix of mom and pop shops, and plenty of room on the large outskirts of town to run around -- it is the second largest town in Massachusetts in terms of square mils -- yet hasn't succumbed to overdevelopment. Also impressive is the Main Street USA look just off the downtown with its concentration of spectacular, big old homes.  On Route 28, check out Dave's Diner, offering great comfort food in a retro 50s diner atmosphere.

Central and North Central Massachusetts

West Brookfield, has one of the prettiest town commons you'll ever see and features summer little league games and concerts, fall events and tree lighting ceremonies during the Christmas season. The entire downtown district is on the National Register of Historic Places and has a few nice stores including the Book Bear used book store, an old-time hardware store and a variety store. It is home to the Salem Cross Inn, a historic Colonial restaurant featuring New England charm and fare, including some delicious prime rib, Yankee pot roast, chicken pot pie, Atlantic salmon, apple raspberry roasted duck, Indian pudding, butternut squash, pumpkins muffins, homemade breads, clam chowder and the amazing pecan pie and apple pies.

Groton has perhaps the most accurate New England look, with two prep schools, a downtown anchored by a classic white church and town common, the Stagecoach Inn and Tavern built in 1768, a beautiful public library and historic old homes. The Natural Market health food store is housed in the former town post office, and there are several area antique shops. Groton also features several apple orchards and farmstands, perfect stops when traveling the rural backroads of New England.

Western Massachusetts/Berkshire Mountains

If you really love old homes, then check out the 330-year-old, mile-long Main Street in Deerfield. It's a spectacular architectural tour of early New England with many homes built in the 1700 and 1800s.  One of the old homes is the Deerfield Inn, built in 1884 and a favorite traditional New England lodging destination. To add some more New England presence, the famous Deerfield Academy graces the Main Street with dignity and an aura of academia.  For those in search of something more modern, the Yankee Candle Company in South Deerfield features more than 160 candle varieties, 16,000 square feet of home furnishings, a candle making museum, foods from fudge to gourmet dinners (and Chandler's Restaurant), a car museum, a Bavarian Christmas Village with themed holiday shops and a 25-foot Christmas tree!

Shelburne Falls cleverly combines the look of a small town -- coffee shop, local pharmacy, book store -- with the presence of upscale galleries and boutiques. With its vibrant, yet laid-back old-fashioned-looking downtown and the amazing Bridge of Flowers -- an old railroad bridge featuring 400 ft. of more than 500 flowers, plants and twigs and a stunning view of the Shelburne River -- this cozy town is truly a nice place to be -- sort of like Mayberry RFD with a bowtie.

Stockbridge, for all its fame, has essentially remained a small town with a peaceful aura and a look that Norman Rockwell so famously captured in his art work. Located in the Berkshire Hills of western Massachusetts, this beautiful valley town features the stunning Red Lion Inn established in 1773, historic mansions, the Berkshire Theater Festival, the old-fashioned and very old Stockbridge Public Library, a working fountain built in 1881, and a 19th century village green. The Elm Street Market confirms the small-town living presence -- it's an old-fashioned standalone market with a counter to grab a meal.

Cape Cod

Welfleet might just be the most unspoiled, attractive small town on Cape Cod. Seventy-five miles out into the Atlantic Ocean, Welfleet is a rural coastal town, with 61 percent of the area being part of the Cape Cod National Seashore Park.  That means great ocean beaches for you to enjoy! The Central Village area represents quaint Cape Cod at its finest with a nice variety of shopping and dining oppoortunities -- it is a great place to stroll. Welfleet also features fresh water ponds and one of the last drive-in theaters in the area. What a great place to vacation, the type of Cape Cod destination you'd expect from this region -- as opposed to the overcommercial areas in other towns that have been changing the area.

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