The 11 Can't-Miss Towns In New England
New England, a region in the northeastern US, is made up of six states, which are Maine, Vermont, New Hampshire, Connecticut, Massachusetts, and Rhode Island. This region has a long and rich history, home to Indigenous People for tens of thousands of years, and later home to some of the earliest Colonial territories, which would become many of the country's first states. New England is characterized by the restorations and preservation of the architecture from many of those ancient eras, many still-functional coastal waterfronts, and incredible scenic beauty, especially vibrant fall foliage. With so much to offer, the small towns in this stunning part of the US truly cannot be missed on your travel itinerary.
Kennebunkport, Maine
A small coastal town on the Atlantic shore of Maine, Kennebunkport is home to only 3,700 residents year-round, but in the summer, this fishing village can have around 10,000 tourists a month. It is known for its beautiful beaches and historic streets lined with restaurants and boutique shops, particularly around its popular Dock Square. Kennebunkport also displays beautiful fall foliage and hosts downtown festivals in the off-season, such as the annual Christmas Prelude. The various attractions make this beach town a favorite for visitors to Maine for well over a century, and it can still not be missed when journeying through New England.
Some Dock Square favorites include eating a lobster roll or fried clams at the iconic dining spot, The Clam Shack, and enjoying a locally crafted beer at Kennebunkport Brewing Company. There are also many fun places to shop and support resident artists, including Good Earth, a highly rated pottery store, and Lupine Books, an independently owned bookstore offering products for every age.
Woodstock, Vermont
In the scenic foothills of the Green Mountains of Vermont, the charming town of Woodstock sits along the Ottauquechee River. This town has a town square called The Green, a quintessential New England covered bridge called the Middle Bridge, and a ton of unique architecture from the 1800s, including the pink sandstone Norman Williams Public Library. In the 1980s, the town gained some fame when a popular movie, Ghost Story, was filmed there. Woodstock is a great place to visit in all four seasons, being another popular spot for fall foliage viewing.
Locals would recommend visiting the Billings Farm & Museum if you are a family traveling with kids, because it is an educational history museum, but it has lots of interactive exhibits which are great for all ages, not to mention cute farm animals. For getting up close to the area's stunning nature, the Marsh-Billings-Rockefeller National Historical Park is a perfect option, with easy and scenic hiking trails and a gorgeous Victorian mansion on the grounds.
Madison, Connecticut
Home to around 18,000 people, the city of Madison lies on the shore of Connecticut's part of the Long Island Sound. It has the best of both worlds as far as landscapes, with an outstanding Atlantic beach, as well as lush woodlands, including the nearby Cockaponset State Forest. It is also near the large and populous city of New Haven, offering a calm, quiet alternative to the bustling bigger town, but with all of the same amenities. Madison has a thriving downtown with numerous entertainment options, parallel to its six miles of pristine beaches.
Popular attractions in Madison include eating a classic New England lobster roll at Guilford Lobster Pound, followed by dessert at Ashley's Ice Cream, which has been voted best in Connecticut. Another beloved local vendor is the independent bookstore RJ Julia Booksellers, which is known for its comfy vibes and for holding author meet-and-greets often.
Provincetown, Massachusetts
A unique town at the tip of Cape Cod, Massachusetts, Provincetown is at the end of a peninsula and is therefore completely surrounded by ocean. Its main drag, Commercial Street, is clustered with art galleries, cafes, and historic inns. The town, a long-time haven for artists, as well as members of the LGBTQ+ community, has a strong presence of Portuguese influence, and is the site of the Pilgrims' Mayflower Landing. This eclectic mix of cultural traits creates a fun and welcoming atmosphere that simply cannot be missed if you are visiting the Cape Cod area.
Along Commercial Street, you will find endless entertainment options, but there are a few that cannot be missed in order to capture this lovely little town's spirit. One is a visit to the Pilgrim Monument & Provincetown Museum, which is not only educational on the history of the town, but also beautiful, as you can climb to the top of the monument for panoramic ocean views. Another noteworthy museum is the Provincetown Art Association and Museum, which has a particular focus on local Provincetown and Massachusetts artists. You can even do something wild and take a Provincetown Ghost Tour!
Littleton, New Hampshire
The quaint mountain town of Littleton, home to 6,000 people, is at the northwest end of the iconic White Mountains of New Hampshire. The town also lies along the Connecticut River, giving it the best of both worlds: water views and mountain peaks. Littleton is well known for being a cheerful place, embracing its nickname of "Glad Town." When you visit its walkable downtown area lined with modern local businesses in restored old buildings, you will feel truly welcomed by the locals.
They might recommend visiting Chutters, a sweet snack staple for tourists with its 112-foot-long candy counter, or The Coffee Pot for a fresh pastry or delicious breakfast sandwich. If you would prefer to drink your calories, Littleton has a couple of local breweries, Schilling Beer Co. and Wildbloom Beer, the former of which is located inside a stunning 18th-century mill. The latter, Wildbloom, is a newer brewery in a more modern spot on Main Street, and they source local ingredients for their craft beers.
Charlestown, Rhode Island
On the southern coast of Rhode Island, the relaxing town of Charlestown combines beautiful outdoor attractions with the laid-back charm of a New England beach town. Unlike some of the more densely populated coastal cities, Charlestown has several less developed barrier beaches that draw visitors for their quiet atmosphere and raw natural scenery. Its downtown is family-friendly with less party-affiliated nightlife, instead being a haven for unique, slower-paced attractions you can bring your kids to.
The most popular of these might be Charlestown Town Beach, a perfect spot to bring the family to for sunbathing, swimming, and relaxing. If you want to go for a hike, Ninigret National Wildlife Refuge has many trails, some of which are easy for all skill levels, and all of which provide tranquil scenery and a multitude of birds and animals unique to the salt marshes there. Charlestown has some unique indoor settings as well, such as the Fantastic Umbrella Factory, which is not actually a factory at all, but rather a neat cluster of shops and local vendors. They also have gardens with fresh fruits and vegetables for purchase, and it is on a farm, so there are cute roaming animals too!
Bath, Maine
The beautiful port city of Bath, on the southwestern coast of Maine, is home to just under 9,000 people. The charming town is steeped in maritime history, known for its long-successful shipbuilding industry, as well as being on the Atlantic Coast and the Kennebec River. It has a lovely downtown area with a ton of preserved 19th-century architecture, and the walkability of its main drag, Front Street, is excellent. Plus, Bath's New England friendliness gives it a warm, small-town feeling, all while it is surrounded by awesome waterfront views.
Shopping on Front Street gives you the opportunity to buy locally made goods, such as gifts, jewelry, and pottery, at Lisa Marie's Made in Maine. Mockingbird Bookshop is another independent boutique with tons of small authors represented on its shelves. They have coffee and tea inside as well. The dining downtown is great too, with a couple of popular options being Bath Brewing Company, a cozy brewpub, and Linden + Front, an upscale spot for American cuisine focused on seasonal ingredients.
Stowe, Vermont
A tiny ski town tucked into a stunning valley in between massive peaks of Vermont's Green Mountains is Stowe, an iconic little New England village that cannot be missed. Mount Mansfield, which is in fact the state's tallest peak, is the town's direct neighbor, and despite being home to less than 1,000 people year-round, Stowe brings in a lot of winter sports enthusiasts annually because of its excellent location. It has even been referred to as the "Ski Capital of the East Coast," but it is a great place to visit any time of the year.
If you visit in the summer, in fact, Stowe has so many scenic areas to go hiking, including the Stowe Recreation Path, which is five and a half miles long and paved, so it is perfect for walking or biking, and surrounded by nature, plus it travels through downtown. Just outside town is Smugglers Notch State Park, packed with more hiking trails, some of which are a little more difficult, winding above and around unique rock formations. After spending your day outdoors, you cannot miss winding down with an ice-cold IPA at a local legend, The Alchemist Brewery.
Stonington, Connecticut
Stonington, a popular coastal city that lies on the Atlantic-fed Long Island Sound that borders Connecticut, includes both its namesake Stonington Borough as well as the historic village of Mystic. Stonington is actually the oldest borough in the state, having been incorporated in 1801, and is well-known for its concentration of restored colonial architecture. It also has a working waterfront and fishing fleet, as well as a lengthy background of maritime success. For people who love museums and lighthouses, this is an essential stop, and you can find both together at the Stonington Lighthouse Museum.
The Velvet Mill is a very unique attraction in Stonington. It is an old textile mill that has been remodeled inside and is now filled with local vendors, selling art, baked goods, craft beer, and more. This city has lots of good drinks, with another highly recommended option being Saltwater Farm Vineyard, serving up award-winning wines in a beautiful location on a 100-acre farm.
Keene, New Hampshire
The Monadnock Region of New Hampshire, known for its namesake mountain and state park, contains many small towns and villages, the largest of which is Keene. It is the county seat, which houses around 20,000 residents, meaning it is still quite small by the rest of the country's standards, and it has a friendly college town feeling to it. Keene is well-regarded for its vibrant downtown, fun and popular annual festivals, including the Keene Music Festival and Monadnock International Film Festival. It is very artsy and has a bunch of galleries and local vendors to enjoy as well.
The most highly rated of those galleries online is Hannah Grimes Marketplace, which showcases many local artists and offers a wide array of unique gifts. Keene has a locally owned movie theater as well, called Keene Cinemas 6, if you are in town but missed the film festival. For dessert, stop by Eat More Cake on Main Street for yummy cupcakes, macarons, and more.
Salem, Massachusetts
While this iconic Massachusetts town is mostly known for its dark history, Salem is noteworthy for many things besides witchcraft. It is also home to a breathtaking rocky coastline, a charming downtown with brick streets and old buildings, a ferry that takes visitors on educational tours, and a ton of local businesses to check out. Many shops are uniquely tailored to people interested in the town's witch trials, like crystal and tarot stores, but there are also a lot of cute little cafes and a diverse food scene, plus the Essex Pedestrian Mall, which has a bunch of unique attractions.
Salem has incredible food options as well, including excellent seafood, being right on the coast. Turner's Seafood, a very popular dinner spot in historic Lyceum Hall, has many positive reviews online, plus the building is said to be haunted. For breakfast, Gulu-Gulu Cafe on Essex Street cannot be missed, offering a global menu and strong coffee. Far From the Tree is another neat stop, a local cider brewery with many delicious and seasonal options.
In the unforgettable small towns of New England...
You truly cannot miss the friendly downtowns, like the one in Littleton, the fun festivals like those in Keene and Kennebunkport, and the family-friendly attractions in towns like Woodstock and Charlestown. New England is also incredibly historic, with places like Salem and Provincetown going all the way back to the 1600s. Each of these small towns will provide you with a quality experience you and your family will never forget!
