The Best Small Towns in Massachusetts

During the three weeks we spent in New England in fall 2012, we visited six states and drove over 1500 miles. It was fast paced and exciting.

I had been looking forward to visiting New England to experience the fall foliage for so long and we wanted to make the most of our time there so we hired a car and hit the road from Boston, one of the largest cities in Massachusetts.

Check out this awesome New England Road Trip Itinerary to help you plan your road trip!

Boston in itself was a massive highlight for me and the ideal city to kick off a year of adventure. I have written a separate post about this amazing city. This post is about the other incredible towns in Massachusetts that we visited.

Because Massachusetts turned out to be my favourite state on this trip and I loved visiting Massachusetts in fall.

Fall colours in Provincetown - one of the best small towns in MassachusettsEverywhere we visited in Massachusetts impressed me, and for different reasons. The diversity of 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 landscapes may vary from western to eastern Massachusetts, but we found it all to be beautiful.

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

The quaint towns in Massachusetts listed below are the reason why I loved the State so much.

The Best Small Towns in Massachusetts

Concord, Massachusetts

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 off lamp posts.

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

Old Town Hall in Concord Massachusetts - Fall colours in Provincetown - one of the best small towns in Massachusetts Beautiful Concord Massachusetts - Old Town Hall in Concord Massachusetts - Fall colours in Provincetown - one of the best small towns in MassachusettsSleepy 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 filtering 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.

Sleepy Hollow Cemetery in Concord Massachusetts - one of the best small towns in MassachusettsClose to the small town centre 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 18th 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.

Old North Bridge in Concord - one of the best small towns in MassachusettsThe 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 back yard instead. There was a reconstruction of the cabin near the parking lot and it really was tiny.

Walden Pond near Concord - one of the best small towns in MassachusettsBack in town, we ate pulled pork burritos 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 we visited.

Inn in Concord - one of the best small towns in MassachusettsSalem, Massachusetts

The small town of Salem, Massachusetts 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 - one of the best small towns in Massachusetts Salem is an attractive harbour-side town with cobbled pedestrian streets, eighteenth century ships in the harbour, 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. We visited the memorial to the victims only.

Mayflower pilgrim grave in Salem - one of the best small towns in MassachusettsSalem Harbour - one of the best small towns in Massachusetts

In a cosy Salem café I had a decadent pumpkin pie and white chocolate latte and we browsed the oldest candy store in US for more sweet treats. Despite the over the top witch stuff, Salem, Massachusetts is a charming historic town full of quirky people. My favourite kind of people.

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

Downtown Salem - one of the best small towns in MassachusettsNorthampton, Massachusetts

I hadn’t heard of Northampton, Massachusetts when planning our road trip but we 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, book stores 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, we 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 us 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.

Smith College in Northampton - one of the best small towns in MassachusettsThe Berkshires

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

A super quaint little town and the birthplace of Norman Rockwell, Stockbridge doesn’t have any chain stores which you don’t see often enough in the United States, a land of rampant consumerism and strip malls.

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

We 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.

Chatham, Massachusetts

Another cold and overcast day was spent in the fishing town of Chatham, located at the south eastern 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.

Downtown Chatham in Cape Cod - one of the best small towns in Massachusetts Pumpkin sale in Chatham - one of the best small towns in MassachusettsWe 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 we enjoyed exploring the bookstores and gift shops in this cute town.

Scarecrow competition in Chatham - one of the best small towns in MassachusettsA bit further out of town is the Chatham Pier where we 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 us every couple of minutes.

Seal in Chatham, Cape Cod - one of the best small towns in MassachusettsOur last stop in Chatham was to the Lighthouse, which overlooked a very windswept beach. Fighting against the howling wind we walked along the long, empty stretch of sand before the wind and cold got too much and we headed back to our motel.

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

Beach in Chatham, Cape Cod - one of the best small towns in MassachusettsProvincetown, Massachusetts

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 centre is full of amazing restaurants, cool cafes, cosy 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 we did on our first evening. There was an old man riding a bike with a transistor radio playing in his basket. He was singing along to a tune from the 60’s while he slowly looped along the wharf then back again.

Beach in Provincetown - one of the best small towns in MassachusettsThe 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 we climbed to the top for fantastic coastal and town views.

Pilgrim Monument in Provincetown - one of the best small towns in MassachusettsWe stayed at the Sandcastle Resort for a fantastic off-season price in a large studio which even had its own kitchenette. After not being able to cook for the preceding two weeks this was massive for us.

The Sandcastle Resort had a Jacuzzi and two pools, which we put to good use, and it was only a five minute drive into town. After mostly staying in budget motels on the outskirts of town during our road trip, this felt like luxury.

All of the food we ate during our two nights in Provincetown was really good but my favourite meal was at The Lobster Pot where we had 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 us. A tall forest of beech trees and scrub pine enclosed a still lake. We 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.

Lake in Cape Cod National Seashore near Provincetown - one of the best small towns in MassachusettsRace Point beach in Cape Cod near Provincetown - one of the best small towns in Massachusetts

Our 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 land fall thousands of miles away.

Highland Light Cape Cod near Provincetown - one of the best small towns in MassachusettsProvincetown definitely cast a spell on me. It is absolutely, positively one of the best places to visit in Massachusetts.

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. We only spent a day on Martha’s Vineyard 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.

I left Massachusetts with still so much to see. We didn’t make it to the oldest city in Massachusetts – Plymouth, we didn’t make it to any of the other major cities in Massachusetts other than Boston, we 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?


The Best Small Towns in Massachusetts

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12 Comments on The Best Small Towns in Massachusetts

  1. I lived in the US Northeast for years and spent so much time in Mass. The Cape is such a special place, and good on you to visit during the off season. That highway is literally torture if you get there on a Saturday in July!

  2. I’m so glad you loved MA! We live in Rhode Island but only a mile from the border with Massachusetts so we spend a lot of time there. We were in the Berkshires last weekend and always visit Provincetown in the summer. I’ve also found Salem to be a very cute town.

  3. I have lied in Massachusetts all my life and though I know there are many beautiful places in the world I have never felt the need to leave Massachusetts as there is a town for everyone of my many moods. I love all of the states in New England and I have been to the eastern provinces I Canada, which I love, for all the reasons I love Massachusetts. I currently live in a small town on the rural campus of Wheaton College. Aside from the ticks, it is my idea of heaven. I even love the snow and other crazy weather.

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