The Best Small Towns in Massachusetts

When people think of Massachusetts, Boston is what usually comes to mind. And I love Boston, but this post is an ode to the best small towns in Massachusetts because they are what charmed me most about the state – especially during fall.

I spent a month in total in New England during fall over a couple of different visits, visiting six states and driving over 1500 miles. It was incredible. Doing a New England road trip is almost a rite of passage if you are a fall worshipper like I am.

Boston in itself was a massive New England highlight for me – the history, the architecture, the food. I have written a separate post about this amazing city. This post is about the other incredible towns in Massachusetts that I have visited.

Because Massachusetts turned out to be my favorite state in New England and I loved visiting Massachusetts in the fall.

Everywhere I have visited in Massachusetts impressed me, and for different reasons. The diversity of the landscape was a big part of it.

From the rolling hills of the Berkshires to the sea salt charms of gay-friendly Provincetown at the tip of Cape Cod (the same place known for the famous chips).

The landscapes may vary from western to eastern Massachusetts, but I found it all to be so beautiful.

With unseasonably cold weather during my first time in Vermont and New Hampshire (it snowed when I was in the Green Mountains!) I ended up spending a lot more time than originally planned in Massachusetts. Something that I ended up being grateful for.

And then I visited a few new places on my second visit and fell for Massachusetts even more.

The small cities and quaint towns in Massachusetts listed below are the reason why I loved the state so much.

The Best Small Towns in Massachusetts

Concord

Concord, Massachusetts is a fairy-tale version of a small New England town: Perfect in every way and so damn quaint it hurts.

Concord is a town full of dignified trees aflame with fall color, grand old inns, and a quiet main street of historic buildings with the stars and stripes proudly displayed above doorways and hanging off lamp posts.

Nothing looked out of place, everything was clean and tidy and colorful. I loved it.

Sleepy Hollow Cemetery in Concord is the final resting place of a number of celebrated authors and poets including Henry David Thoreau, Louisa May Alcott, Nathaniel Hawthorne, and Ralph Waldo Emerson who are buried on a grassy hilltop known as Author’s Ridge in its serene grounds.

Soft afternoon light filtered through the tree canopy and onto the historic stone gravestones as we walked across the spongy carpet of pine needles coating the ground. A quiet sense of contentment washed over me.

I always find cemeteries so peaceful and Sleepy Hollow Cemetery is one of the most beautiful I have ever seen.

Close to the small town center of Concord is the Old North Bridge where the first successful armed resistance to British rule took place in 1775. The current bridge is a replica of the one that stood in the 18^th Century and crosses the Concord River in the same spot.

A grand old dame, Old Manse House overlooks the river and was built by Ralph Waldo Emerson’s Grandfather. An idyllic spot in the Massachusetts countryside.

The main reason I wanted to visit Concord, Massachusetts was to visit Walden Pond, two miles from town.

From 1845 to 1847, the author and transcendentalist Henry David Thoreau lived a simple life in the woods above Walden Pond, during which time he wrote about his experiences in solitude and connecting with nature in his book ‘Walden; or, Life in the Woods.

I wanted to find the spot where his cabin had been but we got lost and ended up in someone’s backyard instead. There was a reconstruction of the cabin near the parking lot and it really was tiny.

Back in town, I ate a burrito sitting by a stream in the sun. It cemented my love for this perfect little town – definitely one of the best towns in Massachusetts that I visited.

Where to Stay in Concord: Stay at the historic Concord’s Colonial Inn in one of their well-appointed guest rooms. Located only 5 minutes from the town center, this 1716 inn has two restaurants on-site.

Salem

Salem is best known for its bloody history, where during the witch trials of 1692-1693 twenty innocent people were put to death.

Salem certainly embraces its dark history now, especially during the month of October when they celebrate Halloween for the full 31 days.

The streets and shop windows of Salem were decorated with fake spiders, corn stalks, jack-o-lanterns, and other spooky paraphernalia and we saw quite a few people walking around in costumes.

The streets were bustling with excited people embracing the most looked-forward to month in Salem.

Salem is an attractive harbor-side town with cobbled pedestrian streets, eighteenth-century ships in the harbor, an attractive cemetery with the grave of a Mayflower pilgrim, refined old buildings, and lots and lots of witch stuff.

In Salem, there are numerous witch museums, a witch trials memorial, witchcraft shops, and the Witch House where one of the magistrates lived and where the preliminary examinations of the accused were held.

It’s all a bit much considering that the people that were tortured and murdered weren’t witches, but were just unfortunate enough to be condemned by a group of hysterical girls. I visited the memorial to the victims only.

In a cozy Salem café, I had a decadent pumpkin pie and white chocolate latte and browsed the oldest candy store in the US for more sweet treats.

Despite the over the top witch stuff, Salem, Massachusetts is a charming historic town full of quirky people. My favorite kind of people.

Needless to say that Salem is one of the more interesting places in Massachusetts.

Where to Stay in Salem: Stay at The Merchant Hotel or the Daniels House Bed and Breakfast – both of which are in central Salem and close to many of the city’s attractions. 

If you prefer a vacation rental, stay at this 1739 historic cottage in downtown Salem.

Northampton

I hadn’t heard of Northampton, Massachusetts when planning my road trip but I happened to pass through it on the way down from Vermont and decided to stop for lunch.

Northampton is a lively college town, the Women’s College Smith has its campus here, and the town is full of cool cafes, bookstores, and talented buskers performing in the street.

Northampton, Massachusetts has a vibrancy about it that was perfectly accentuated in the fall sunshine. I had been feeling fatigued and uninterested all morning but on arrival in Northampton, I felt invigorated.

After eating cheap and unhealthy food for days, I had an amazing healthy lunch at a mainly vegetarian restaurant on Northampton’s main street. Eating a vegetable and tofu stir-fry with roasted pumpkin and apple cider made me finally feel nourished.

The grounds of Smith College were stunning and a great place for a wander with weeping willows, grand old buildings, and majestic trees with beautiful fall foliage.

Walking around a still lake with squirrels bounding through the trees above me made me feel ensconced in nature and where we were supposed to be.

I loved my short time in Northampton – one of the most vibrant and cool places in Massachusetts.

Where to Stay in Northampton: Stay at the centrally-located and historic Hotel Northampton, or The Ellery, a stylish hotel close to downtown.

For vacation rentals, stay at this spacious bamboo studio, the Noho nest tiny studio downtown, or this mountain view apartment.

Old Sturbridge Village

Located in the town of Sturbridge, Old Sturbridge Village is a 200-acre living history museum that recreates life in rural Massachusetts between the years of 1790 to 1840.

Even though it is not really a small town, I had to add it to the list as I loved my visit there and it definitely feels like a real village – albeit one from the past.

You could easily spend a day in Old Sturbridge Village, watching all the wonderful old skill demonstrations from shoemaking to blacksmithing, checking out the historic buildings that were brought to the village from all over New England, and just enjoying the gorgeous natural environment the village is set in.

After a long day in the village, grab some beers at a nearby local icon, Tree House Brewing Company, which has a wide range of excellent beers.

Where to Stay in Sturbridge: Stay at the Publick House Historic Inn and Country House, only a mile from Old Sturbridge Village and surrounded by beautiful New England countryside. The Hamilton Inn Sturbridge is another great option in the area.

The Berkshires

After good weather for most of my time in Massachusetts, my luck ran out when I reached the rolling hills of the Berkshires. I didn’t get to explore the countryside with its famed fall colors because of the weather, but I liked what I saw in the small town of Stockbridge, where I stayed for an evening.

A super quaint little town and the home of Norman Rockwell for the last 25 years of his life, Stockbridge doesn’t have any chain stores which you don’t see often enough in the United States.

The stately Red Lion Inn in Stockbridge is the focal point of the town and I would have liked to eat there but it was fully booked for the whole evening.

I only had a small glimpse into this pretty part of Massachusetts and I will certainly return one day (hopefully with better weather) to explore the more natural pursuits in the area, as the fall colors are meant to be spectacular here.

Where to Stay in The Berkshires: Stay at the most iconic inn in The Berkshires – The Red Lion Inn in Stockbridge in one of their unique and luxurious rooms. 

For vacation rentals, stay at this private rustic cottage with lake access, this A-Frame in the forest, or this Berkshire Village Carriage House.

Newburyport

On my most recent visit to Massachusetts, I spent an evening exploring beautiful Newburyport, a small coastal city in northern Massachusetts, just south of the New Hampshire border.

Newburyport is known for its historic seaport and the area around the harbor and State Street is a great place to go for a stroll and admire the history of the town.

Don’t miss the oysters and the hot lobster roll at Sea Level Oyster Bar – it was the best lobster roll I have ever had and Toby LOVED their oysters.

Where to Stay in Newburyport: Stay at the Compass Rose Inn, a bed and breakfast located minutes from the waterfront on a quiet lane, or the historic Essex Street Inn & Suites.

Chatham

Another cold and overcast day was spent in the fishing town of Chatham, located at the southeastern corner of Cape Cod. A charming town even under grey clouds, all signs pointed to Chatham being a close-knit community.

With community notices outside local businesses and friendly locals chatting to one another on the street, I bet Chatham is a lovely town to live in.

I checked out the scarecrow competition on display at the town park where local businesses were competing against each other. Some of the entries were very imaginative and I loved the homage to ‘The Nightmare before Christmas’.

There was a pumpkin patch outside the church on Chatham’s Main Street and I enjoyed exploring the bookstores and gift shops in this cute town.

A bit further out of town is the Chatham Pier where I went to visit the local seals hanging around, hoping for a fisherman to give them some of their catch.

They were cheeky things and were very curious about us, swimming a little way off the pier but sneaking looks at me every couple of minutes.

My last stop in Chatham was to the lighthouse, which overlooked a very windswept beach. Fighting against the howling wind I walked along the long, empty stretch of sand before the wind and cold got too much and I headed back to our motel.

There were lots of things to see in do in Chatham, another of my favorite small towns in Massachusetts.

Where to Stay in Chatham: Stay at the Queen Anne Inn with secluded grounds and a pool, Captain’s House Inn in a historic sea captain’s estate, or The Hawthorne Motel with oceanview rooms.

For vacation rentals, stay at this cute studio cottage, or the Captain’s Haven Cape Cottage.

Provincetown

In my opinion, the most beautiful place in Massachusetts is Provincetown, located at the tip of Cape Cod. Provincetown is a gay-friendly hub of gentrified prettiness but with flair. Gorgeously maintained houses with flower-filled backyards and colorful trim are home to a multitude of B&Bs.

Colorful pride flags wave from lamp posts and the vibrant town center is full of amazing restaurants, cool cafes, cozy bookstores, and trendy galleries.

The Provincetown pier is a great spot to sit in the pre-sunset hours to while away time before dinner which I did on my first evening.

The granite Pilgrim Monument sits above town and commemorates the landing of the Mayflower pilgrims in 1620 as Provincetown was their first stop before sailing on to Plymouth when they couldn’t find a water source.

The Pilgrim Monument is the tallest granite structure in the US and I climbed to the top for fantastic coastal and town views.

All of the food I ate during my two nights in Provincetown was really good but my favorite meal was at The Lobster Pot where I shared scallops au gratin, lobster in brandy cream sauce, red potatoes, and corn cobs. The best lobster I have ever had.

Provincetown, Massachusetts is surrounded by sand dunes, white sand beaches, and forest that make up part of the protected Cape Cod National Seashore. At the Visitor Centre, there is a fantastic viewing deck over the dunes and coastline.

While hiking a 5.5-mile walk through the dunes and forest, small black and white birds darted at my head when I called them.

Undulating dunes surrounded me. A tall forest of beech trees and scrub pine enclosed a still lake. I walked through the powdery white sand dunes of Race Point Beach and I wished it was summer to fully enjoy it.

With everything it offers, Provincetown has got to be one of the best places to live in Massachusetts.

My last sunset was at the lonely Highland Lighthouse in nearby North Truro. Perched high above the roaring Atlantic, the lighthouse looked out onto an expanse of ocean with the next landfall thousands of miles away.

Provincetown definitely cast a spell on me. It is absolutely, positively one of the best places to visit in Massachusetts.

Where to Stay in Provincetown: I stayed at the Sandcastle Resort which has large studios with kitchenettes, a jacuzzi, and two pools. Another great option is the chic Breakwater Hotel.

For vacation rentals, stay at this one-bedroom cabin on a historic fishing wharf, this 1920s tiny house cottage, this charming west end cottage, or this spacious modern cottage.

Martha’s Vineyard

Not exactly a small town – Martha’s Vineyard is a large island – it is amazing nonetheless and one of the most beautiful places in Massachusetts.

I only spent a day on Martha’s Vineyard visiting the small towns of Vineyard Haven and Oak Bluffs, but it is definitely somewhere I would like to return to in summer to truly experience the island’s charms.

I’ve already written about my time on this idyllic island, you can find my post about it here.

Where to Stay on Martha’s Vineyard: Stay at Isabelle’s Beach House, an oceanside bed and breakfast in Oak Bluffs, the Victorian-style Pequot Hotel in Oaks Bluffs, or The Sydney, a colorful inn in Edgartown.

For vacation rentals, stay at this adorable cottage in Oak Bluffs or this studio in a Victorian Sea Captain’s home in Vineyard Haven.

I left Massachusetts with still so much to see. I didn’t make it to the oldest city in Massachusetts – Plymouth, I didn’t make it to any of the other major cities in Massachusetts other than Boston, and I didn’t make it to nearly enough Massachusetts coastal towns. There are still so many cool places in Massachusetts to experience.

Massachusetts is a special state with so much to offer visitors, whether you love cities or nature. It really has it all. And the heart of this state is found in its small towns – the best places to visit in Massachusetts.

Have you been to Massachusetts? What do you think are the best places in Massachusetts?

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