10 Places To Love When You Visit Boston, Massachusetts

I have a long-standing love affair with the United States, having grown up on a regular diet of American TV shows and films as a child in the 1970s and 80s. As a result, we have visited quite a lot as a family, discovering great variety across the States, and checking out its iconic cities – New York, New Orleans, LA, San Francisco, and Chicago. Each has its own character, and each is lovable in its own way, but now I’ve had the chance to plan a visit Boston, I have been won over. Here are 10 places in Boston that stole my heart…

1. Charles Street, Beacon Hill

We stayed in a boutique hotel on Charles Street in the historic Beacon Hill neighbourhood of Boston. The name Beacon Hill comes from a signal beacon once placed on the hill to warn inhabitants of danger, although these no longer exist.

Charles Street is a smart row full of handsome red brick buildings, boutique shops (for books, clothes, leather goods and nuts!) and eateries. When we visited in late September, the hilly side streets were lined with trees changing colour and the Autumnal window displays were tasteful and enticing.

Finding breakfast on Charles Street wasn’t a challenge, with lots of great options such as Cobblestones Café and Tatte Bakery, full of pastry delights and things with lots of calories.

If you’re in the Beacon Hill area, then head to Acorn Street to see one of the prettiest streets in Boston with cobblestones and gas lamps on a row of Federal style houses. It was built in the 1820s for artists and tradespeople – lucky them!

ALTERNATIVE – Boston is a city of neighbourhoods, 23 in fact, so there are plenty to explore, and you might find one that you prefer when you visit Boston. Try to make time to check out North End, Back Bay, Fenway-Kenmore and Charlestown on your first visit to Boston.

2. Beacon Street Brownstones

Walking from the hotel on Charles Street to the Fenway-Kenmore area, we wandered slowly along Beacon Street, taking in the lines of attractive brownstone buildings. Many of these impressive houses had decorated their doorsteps (stoops) with ‘Autumnal holiday displays’ of pumpkins (orange and green of all varieties) and coordinated foliage.

It was late September when we visited so I would imagine that if you visit Boston closer to Halloween, the house displays would be even more impressive.

Further along we came to an area of Frat houses belonging to Boston University, each proudly displaying their greek names.

ALTERNATIVE – for more incredible doorstop and house displays in the Fall, take a day trip on the train from Boston to Salem only 30 minutes away. Learn about the dark history of Salem on a walking tour, and enjoy the historic buildings and smart streets.

3. The Freedom Trail

Starting from Boston Common in the Beacon Hill area, you can follow the historic Freedom Trail around the city which links key sites and buildings relating to the American Revolution. We walked part of the Freedom Trail under our own steam and relied on guidebooks and information boards for insights, however you can pick up a guided tour from the Visitor Centre or take a narrated Trolley tour if you prefer.

I am a novice historian but found the Freedom Trail extremely interesting. You can’t help but feel the history seeping in as you explore the trail.

ALTERNATIVE – Rather than walking the Freedom Trail, when you visit Boston you could head to the Boston Tea Party and Ships Museum on the waterfront to learn about one of the key events of the American Revolution. At the museum you can enjoy throwing your own crates of tea into Boston Harbor from a replica tea clipper!

4. Mike’s Pastry, North End

North End in Boston was settled by Italian immigrants in the 20th century and today the neighbourhood feels like a ‘little Italy’. You can enjoy a walk around the streets decorated in the Italian colours of red and green, enjoy a stand-up expresso, or find a cosy pizzeria for lunch. However, leave room for a desert Mike’s Pastry, famous for their cannoli.

Queuing up at Mike’s gives you chance to peruse the extensive menu with an overwhelming list of flavour options. Then, when you’ve chosen, the server will package your cannoli in white boxes with blue writing and wrap it up in string from the blue balloons hanging from the ceiling.

ALTERNATIVE – The main competitors to Mike’s are the nearby Modern Pastry Shop, and Bova’s Bakery, both in North End. Everyone seems to have their favourite cannoli outlet. Which will be yours?

5. The Emerald Necklace

The Emerald Necklace is a 16-mile chain of parks and waterways running through Boston, designed by landscape architect Frederick Law Olmsted. There are six major parks in the ‘necklace’ including: Back Bay Fens, the Riverway, Olmsted Park, Jamaica Pond, the Arnold Arboretum and Franklin Park.

We walked on shady, treelined paths through the Back Bay Fens, discovering well-tended allotments belonging to the Fenway Garden Society, and a busy sports field full of school kids playing baseball. It was a haven of tranquility in the city centre, with just the ducks and a few joggers for company.

ALTERNATIVE – in addition to the Emerald Necklace, there are plenty of other green spaces in Boston, such as Boston Common, America’s oldest public park, and the Boston Public Garden with its famous swan boats. If you want to keep fit when you visit Boston, then there were plenty of joggers making the most of all the green spaces, and a Sunday morning fun run on Boston Common.

6. Isabella Stewart Gardner Museum

This is a very special museum in the Fenway-Kenmore neighbourhood, once the home of wealthy Isabella Stewart Gardner, who collected art and items from her travels over 40 years. In this time, she built up and incredible collection of paintings and artefacts from around the world, which she wanted people to see in situ after her death.

So, her stunning four-story house was opened to the public, and every inch of the walls is covered with object d’art. In fact, the building itself is a work of art – built in the style of a Venetian palazzo with a large, plant-filled courtyard in the centre. It is extremely pretty and the amount of art packed in is staggering (over 2,500 pieces). Note – book your tickets in advance as unsurprisingly this is a very popular museum.

ALTERNATIVE – if you still have an appetite to see more art when you visit Boston, head to the Museum of Fine Arts (MFA) for an incredible array of Monet, Gaugin, Rembrandt and Van Gogh masterpieces, also in the Fenway-Kenmore neighbourhood.

7. Fenway Park

The oldest and most storied baseball ground in the United States, Fenway Park has been the home to the Red Sox team since 1912. When you visit Boston, book a tour of the Fenway Park stadium before watching a game, or simply settle in to watch a game from the historic green stands. There’s a great atmosphere at Fenway Park and it’s fun to experience a piece of American culture. Note – you might want to take a cushion for the old seats of the Grandstand, which date to 1934 and have no padding, all part of the experience!

ALTERNATIVE – Bostonians are sport mad and so there are lots of live sport options to choose from. Depending what season it is when you visit, you could book tickets to a Boston Bruins ice-hockey game.

8. Newbury Street, Back Bay

Back Bay is an area of the city reclaimed from swampy land. Today it’s an affluent area of Boston with a bustling shopping street called Newbury Street running through the middle. Newbury street is a wide avenue lined on both sides with designer boutiques and restaurants – great for window shopping or making a few purchases, before stopping at Stephanie’s on Newbury with patio seating for lunch and ordering a bespoke Bloody Mary from their menu of options. I recommend adding bacon and jalapenos!

ALTERNATIVE – if you’ve tired of shopping then, head to the famous Boston Public Library on nearby Copley Square. You may have seen it in the movies?

9. Boston Harbor

I do love a city on the water, and Boston is surrounded by water – both the Charles River and estuary of Massachusetts Bay. We enjoyed a stroll along the Harborwalk from Christopher Columbus Waterfront Park to the Boston Tea Party and Ships Museum, passing Long Walk, several small marinas and boats of all shapes and sizes. We also watched the planes landing at Boston Logan International Airport on the horizon across the water, which felt strange to see so close to the city.

If you want to get out on the water when you visit Boston, then you can take a ferry to the Boston Harbor Islands or take a whale watching boat trip if the season’s right.

ALTERNATIVE – head to Charlestown to visit the USS Constitution and Charlestown Naval Yard, before visiting the Bunker Hill Monument (the end of the Freedom Trail, if you haven’t got here earlier).

10. New England

Boston sits in the New England region of the United States and is the perfect location from which to explore Massachusetts as well as the other New England states – Maine to the northeast, New Hampshire to the north and Vermont to the northwest, Rhode Island, and Connecticut to the south.

With excellent transport links, Boston is a great starting point for a New England Road trip, and a resultant trip combing city, coast, and mountains.

In an attempt to visit all six New England states, we divided our New England states into two separate trips:

• the first one a loop from Long Island, New York, to Connecticut and Rhode Island before passing into west Massachusetts.
• the second one a loop from Boston, Massachusetts, to Southern Maine, into New Hampshire and over to Vermont.

Bonus – Boston has the added benefit of being one of the closest US destinations to reach from the UK (7 to 8 hours and faster on the way back due to the assistance of the Gulf Stream). So, it’s relatively easy to visit Boston from the UK.

We spent 3 days in Boston before heading off on our leaf peeping road trip, but I would have been perfectly happy to have stayed longer. It was smart, attractive, interesting, and felt safe and comfortable. Here’s to the next time!

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