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Historic Towns, Cities and Other Places in New England Not To Be Missed

Article and photos, unless otherwise noted, by Eric Hurwitz. Article updated on 2/10/2019.

Historic Boston Common, Boston, Mass.
Boston Public Garden, Boston.

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New England offers a remarkable concentration of preservation in its communities. Unlike other parts of the country where you have to travel miles and miles of strip malls and faceless condos, New England has an innate respect for history including its Colonial homes, buildings, town commons, churches, and farms.

Although New England has seen its share of cookie cutter enterprises threatening our blessed landscape, there's still enough old-time character to make the six state region unique and unforgettable. Here are some of my personal favorite historic New England towns, cities and other places that you should definitely check out...

Stonington Borough, Conn. (Founded 1649)

Stonington Borough, Conn.

Stonington Borough, Conn.

Picture yourself in Stonington Borough where the old sea captains homes are right up on the front sidewalk and the local mom and pop shops and restaurants are housed in old, well-maintained buildings shaded by trees near the sea. For some reason, Stonington Borough is not as well known as the most popular historic New England towns and cities in new England but every bit as nice if not nicer. Call it your own secret discovery!  Read more on Stonington Borough

Newburyport, Mass. (Founded 1764)

Downtown Newburyport, Mass.
Downtown Newburyport.

Coastal Newburyport  is a wonderfully restored small city with brick sidewalks and buildings that now house interesting little shops and wonderful restaurants. High St. offers some incredible and plentiful examples of Federalist architecture. The look of historic brick, old homes and coastal views lend a vibe that can only be New England. Read more on Newburyport
Stay at a historic Newburyport inn

Weston, Vt. (Incorporated 1799)

Town green in Weston, Vt.
Town common in Weston.

Imagine being in Weston where the whole town is listed on the National Register of Historic Places. It's a great place to admire the old homes, tour the local shops including the famed Vermont Country Store and for, culture, taking in a show at the Weston Playhouse. The small but beautiful town common is a quintessential New England sight to behold (pictured above). Read more on Weston
Stay at a historic Weston inn

Providence, R.I. (Founded 1636)

College Hill in Providence, R.I.
College Hill, Providence.

Newly revitalized Providence has not forgotten its past as Benefit St. contains the largest concentration of Colonial homes in the United States. The rest of the College Hill area -- home to Brown University and the Rhode Island School of Design -- follows suit with one street after another of big old homes and leafy college neighborhoods. Read more on Providence
  Stay at a historic Providence hotel

Historic Deerfield Village, Mass. (Founded 1677)

The Deerfield Inn in Historic Deerfield MA.
Deerfield Inn, Deerfield.

Deerfield is like the rural version of Benefit St. in Providence as this historical New England town has a mile of Main St. homes -- around 80 originally built in the 18th and 19th century. Most prominent are the Deerfield Inn, a charming-looking 1884 inn, and the Deerfield Academy, a renowned coeducational boarding school. Be sure to take a guided or self guided tour to learn what life was like back in Colonial times. Read more on Deerfield

Wickford Village, R.I. (Founded 1637)


Historic Wickford House, Wickford Village, R.I.
Main Street home in Wickford Village.

Wickford Village dates back to 1769 and features the largest concentration of owner-occupied Colonial and Federal homes in the United States. It's a beautiful section of North Kingston, filled with more than 50 shops, nice restaurants and refreshing coastal views. Wickford Village is also a huge "arts" town!  Read more on Wickford Village 

Newfane Village, Vt. (Founded 1774)

Historic Newfane Village, Vt.Charming Newfane Village.

Perhaps the most classic traditional Vermont town, Newfane Village consists of a classic town green, the famous Four Columns Inn, churches with tall white steeples and some of the most beautiful old homes you'll ever see. Most of Newfane Village is listed on the National Register of Historic Places with more than 60 buildings in the Historic District. Greek architecture is the most dominant type of architecture in this charming town. Read more on Newfane Village

Dover, N.H.(Incorporated 1623)

>Downtown Dover 52.JPG
Dover, N.H. By Jon Platek - Own work, CC BY-SA 3.0, Link

The otherwise urban small city of Dover features the William Damm Garrison 1675 House (New Hampshire's oldest intact Garrison house) located at the Woodman Institute on 182 Central Ave. The city is one of my personal favorites as there is no air of pretentiousness and the downtown keeps getting better every day with new stores and restaurants coming in, as well as various beautification projects making things all the much better. Dover is the oldest settlement in New Hampshire! 
Read more on Dover
Stay at a historic Dover inn

Portsmouth, N.H. (Founded 1630)

Downtown Portsmouth, New Hampshire

Downtown Portsmouth, N.H.

Nearby Portsmouth has the 10-acre Strawberry Banke, an outdoor museum of sorts, where you can tour 42 buildings dating back to 1695. The downtown is  surely one of the most impressive in New England, combining a historic small town look with big city amenities (many restaurants, stores, culture). It's a wonderful walking town (city). Read more on Portsmouth Stay at a historic hotel near Portsmouth

Pawtuxet Village, R.I.

Pawtuxet Village, R.I.
Pawtuxet Village, Warwick side.

As one of New England's oldest communities, Pawtuxet Village actually spans two Rhode Island cities: Cranston and Warwick. Many older homes are beautifully preserved and the presence of a falls and cove not too far from the ocean lend a refreshing coastal feel. Pawtuxet Village has recently become a foodie destination, of sorts, with several excellent restaurants gracing the quaint village. Read more on Pawtuxet Village

Old Wethersfield, Conn. (Founded 1634)

Joseph Webb and Isaac Stevens Houses - Wethersfield, CT - 2.jpg
By Daderot - Own work, Public Domain, Link

Located off the manic Silas Deane Highway outside of congested Hartford, Old Wethersfield, founded in 1634, feels like a million miles away from the hundreds of thousands of people that live in this region. Named by "Old House Magazine" as one of the nation's best "old house" neighborhoods, Old Wethersfield has 50 houses predating the Revolutionary War, 100 going back before the Civil War and an additional 150 homes before the turn of the 19th century! These aren't your basic, old run downs homes; most have been extremely well-preserved. Add a leafy look to the village, a classic village green, and a nice downtown Main Street with antique stores, galleries, a tavern and cafe, and you have a perfect, little village that reminds you that you are officially in New England. Read more on Old Wethersfield

Boston, Mass. (Founded 1630)

Acorn Street, Beacon Hill in Boston, Mass.

Acorn St., Beacon Hill in Boston.

Where does one begin with the history of Boston? The history is so rich. I'd start with a tour of the Freedom Trail, which comprises historic museums, meeting houses, burying grounds, parks (including the Boston Common with the spectacular Public Garden), ships and historic markets. Boston is truly one of the great cities of the world -- you'd be hard-pressed to find a city that offers such a wonderful combination of the historic and modern. Read more on Boston

Stay at a historic Boston hotel

Portland, Maine (Founded 1786)

Port Exchange in Portland, Maine

Old Port District, Portland.

I remember Portland, Maine being underwhelming in the 1970s -- too many run-down areas and not enough to do. Years later, it is one of the most likable cities in New England. An incredible effort to revitalize has made the city a destination, as well as a desirable place to live. Particularly impressive is the Old Port District with its shops, restaurants, cafes and car on cobblestones streets with beautiful 19th century brick buildings everywhere you look. What a difference a few decades makes! Read more on the Old Port District

Stay at a historic Portland inn

Lexington and Concord, Mass. (Founded 1713, 1635)

Lexington, Massachusetts in front of the Buckman Tavern

Entertainment in front of the Buckman Tavern in Lexington.

It goes without saying that Lexington and Concord played a major role in the birth of our country. Today, these two historical New England towns are beautiful Boston suburbs, both with a strong sense of historical preservation. Make sure to walk both quaint historic downtowns with plenty of shops and restaurants, as well as Minute Man National Historical Park which commemorates the opening battle in the American Revolutionary War through structures and battlefields. Read more on Lexington and Concord
Stay at a historic Concord inn

Bristol, R.I. (Founded 1680 as part of Plymouth MA county)

Linden House in Bristol, Rhode Island

Historic scene in Bristol.

Bristol features a downtown listed on the National Register of Historic Places. Beautifully-tree-shaded and with lots of great dining options and small town stores, you'll find a remarkable historical concentration of "commercial enterprises, civic buildings, churches, mills, sailors' shacks and slave-traders' mansions," as stated by the National Trust for Historic Preservation. Also check out scenic, expansive Colt State Park and Coggeshall Farm where you'll learn about traditional agricultural practices in a series of historic buildings. South of town is the  45-room English-style manor, Blithewold, considered New England's finest garden estate. Read more on Bristol  Stay at a historic Bristol bed and breakfast

Newport, R.I. (Founded 1639)

Thames St., Newport, R.I.

Thames St. in Newport.

Newport is known for its mansions, ocean, bustling downtown, the Cliff Walk oceanside walk, Newport Folk and Jazz Festivals and America's Cup annual sailing regatta. It's a world-class vacation destination that somehow has held onto its leisurely feel and historical integrity despite all the tourist growth. It's a must-see small city when visiting New England. Read more on Newport

Stay at a historic Newport hotel

Plymouth, Mass.(Founded 1620)

Plymouth, Massachusetts

Approaching downtown Plymouth.

Yes, we all know that Plymouth is the place that the Pilgrims landed in 1620. Nearly 400 years later, the Pilgrim Culture is dominant in Plymouth with Plimoth Plantation outdoor museum, Plymouth Rock, the Mayflower II (a replica of the famous ship) and Pilgrim Hall Museum, but the town is so much more than just that.  Main Street is lively and full of shops and restaurants while parallel Water St. features beautiful Plymouth Harbor and numerous seafood restaurants. The feeling is laid back and friendly, more like a small town than a city. Add some stunning sea captains homes and you've got one of the nicest, most interesting walking towns in all of New England. Read more on Plymouth

Stay at a historic Plymouth bed and breakfast

North Easton, Mass. (Founded 1725)

North Easton, Massachusetts

Ames Free Library and Oaks Ames Memorial Hall in North Easton.

As part of Easton, North Easton Village was settled in 1694, incorporated in 1725 and later became famous for the Ames Shovel Company. The Company provided shovels for the Union Pacific Railroad which opened the west! Oliver Ames was perhaps the best-known of the family -- he was the Massachusetts governor from 1887-1890. But it was famed architect H.H. Richardson who gave North Easton Village its "look," with late 19th century Romanesque-style buildings like the Ames Free Library (currently being renovated), Oaks Ames Memorial Hall (for meetings), The Old Colony Railway Station (current home of the Easton Historical Society) and the Ames Gate Lodge (I think it is still owned by the Ames Family). Beautiful churches complement the area including the Gothic revival style of the Ames built Unity Church. Read more on North Easton

Chatham, Mass. (Founded 1712)

Chatham, Cape Cod Massachusetts
Downtown Chatham scene.

People visit Chatham for the ocean and seafood, but also love the quaint historical Main Street ambiance with more than 300 historic properties in the Olde Village National Register Historic District. There is no nicer Cape Cod town! Read more on Chatham
Stay at a historic Chatham inn


Littleton, N.H. (Founded 1784)

Historic downtown Littleton, N.H.

Downtown Littleton.

Littleton, a historic New England mill town beautifully situated at the edge of the White Mountains near Vermont, could have been just another dying New England industrial community but, fortunately, has employed a vision to make the most of its modest, rural location.

The downtown is surely one of New Hampshire's best examples attracting businesses that have ultimately attracted visitors and pleased residents looking for a full service town center. With a movie theater, toy and book store, Chutters candy shop, a classic in town diner aptly called the Littleton Diner, a furniture store, a post office filled with character, a 100-year old Opera House, the historic Thayer's Inn and restaurants popping up all over the place, Littleton is more than a stop along the way. It's, on one hand, picturesque with its typical New England big, white churches and mountain views, and on the other, a town with a downtown that has nearly all of its storefronts filled -- unusual in this tough economy. There's also a new walking bridge that provides residents and visitors a scenic downtown river walk. Coming from the green, but often regressing suburbs of Boston, we thought, "Why can't we have a downtown like this?"

Littleton, in fact, has done such a great job with its town center that in 2003, The National Trust for Historic Preservation’s National Main Street Center recognized Littleton for its outstanding achievement in the revitalization of a downtown! Stay at a historic Littleton inn

Essex, Conn. (Probably settled in 1648)

Essex CT Griswold Inn 04 (9365849358).jpg
Essex, Conn. By Joe Mabel, CC BY-SA 3.0, Link


A former shipbuilding town dating back to the 1600s, Essex looks refined and perfectly manicured today, but that polish doesn't take anything away from its authentic historical New England small town look and feel. With the old, sprawling Griswold Inn (one of the oldest continuously operated inns in the country) as one of its "anchors," Essex has a timeless quality that hasn't pandered to modern chains and cookie-cutter architecture. What's more, there are 14 miles of sidewalks that allow you to stroll through this relaxing, picturesque community. Essex has all the small town bells and whistles required to make it a special vacation destination: a tree-lined downtown with specialty shops and restaurants, big old historic homes up near the sidewalk,, and a pleasing park with gazebos and picnic benches leading to wonderful, relaxing views of the Connecticut River. Read more on Essex


Related story: Why I love New England




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