10 ways to spend a long weekend in Boston

Home to the world’s most famous baseball team (The Red Sox), the capital of Massachusetts won me over in a long weekend and made me wonder why I didn’t stay for longer!

This Summer I travelled to Boston to visit a friend from University. I know you’re supposed to visit Boston in the fall but I wanted to visit for my birthday. If you can handle the heat then Summer was a wonderful time to visit and soak up the sun by the river and in the parks like the locals!

Charles River Esplanade

I visited New York a few years ago at a similar time of year, but the atmosphere in Boston is far more laidback and easy going. Although there is plenty to do here and to keep you occupied, I took my time to really enjoy the adventures I did have! Read on for 10 ways to spend a long weekend in Boston…!

1. Take a walk through history on The Freedom Trail

Possibly the most famous Boston landmark (or rather series of landmarks), The Freedom Trail is a 4km walk through central Boston that takes you past 16 historic sites within the city. The whole trail is self guided (follow the markers along the roads) and you can choose to walk the whole route or jump on and off sections off it as you make your way round the city (I took a short cut to skip some sections!). At the Granary Burying Ground look out for the narrow skinny house opposite the entrance which is rumoured to be a spite house.

2. Support the Red Sox at Fenway Park

Evening at Fenway Park
Watching the Red Sox at Fenway Park

The Boston Red Sox could be the most famous baseball team in the world and their home ground at Fenway Park is the oldest Major League Baseball park in the US. Attending a match is as much of a social occasion to Boston residents as watching the game itself so if you find yourself in town when they’re playing try and grab a ticket! The atmosphere was great fun even if I had not clue what was happening and turns out baseball is a way slower game than the Wii makes it out to be!

3. Photograph the charming streets of Beacon Hill

The most photographed street in America

It’s not hard to see why Beacon Hill is one of the most sought after areas to live in Boston. With cobbled lanes, gas lamps and orange brick town houses it’s the perfect place to get lost. Acorn Street is at the heart of Beacon Hill and google proclaims it as the most photographed street in America. Unfortunately it seems someone was having some work done on their house when I was there so hopefully you get a clearer view!

4. Relax on Boston Common

South of the Beacon Hill residential area lies Boston Common. Here the city seemed to meet and merge on the grass as people shouted and laughed whilst children played. In Winter, the Frog Pond becomes a skating rink.

Across the road is the Boston Pubilc Gardens where you can see the utterly charming statue ‘Make way for ducklings’ and you can also take a ride on the infamous swan boats.

5. Take the metro out to Cambridge and Harvard University

Barack Obama, Matt Damon, Bill Gates and Natalie Portman are just some of Harvard’s most notable alumni. A metro to Cambridge only takes around 15 minutes from central Boston and you’re transported into the midst of America and the world’s most intelligent students. Although not as old as Oxford and Cambridge universities, Harvard has many beautiful buildings to explore. Harvard Yard is where you’ll get a good feel for the University but for some quiet away from the crowds, head along Brattle Street towards Longfellow House and you’ll pass Radcliffe Square. This is a quieter alternative to Harvard Yard to take a break in!

Plus, if tea is your thing then be sure to check out DAVIDs TEA at Harvard Square for the most amazing selection of teas. I came away with an Aperol Spritz tea…yummy!

6. Savor brunch at Tatte

Tatte is a brunch institution in Boston. And it’s beautiful. The smell of freshly baked pastries makes your mouth water and the menu is so extensive it’s very hard to choose what to have and not just pick one of everything! The smell of freshly baked pastries There are several locations to choose from but the queue is always out the door on a weekend, wherever you go. We visited the Beacon Hill store and had about a 20 minute wait. Worth it.

7. Marvel at the iconic Boston Public Library

The interior of the Boston Public Library is stunning. Keep quiet as you enter Bates Hall, the most famous room in the library, with its striking green lamps. Up on the third floor you can view John Singer Sargeant’s mural The Triumph of Religion covering the walls. For a pit stop and respite from the sun, enjoy a refreshing drink in the peaceful courtyard. Or if you’re visiting in the Winter, enjoy a hot drink in the map room cafe.

8. (Window) shop til you drop in Back Bay

In the late 1800s the area to the South of the Charles River was filled in to create Victorian brownstones houses as is known as Back Bay. This is a fashionable part of town and no street exemplifies this more than Newbury Street which is lined with designer boutiques and chic cafes. Make a stop at Georgetown Cupcake for an exquisite treat to keep your energy up!

8. Stretch your legs along the Charles River Esplanade

The Charles River slices Boston in two and is a great place to cool down with the breeze from the water after the oppressive heat of the city. You can stroll or cycle along the Charles River Esplanade to enjoy the riverside views. Towards Longfellow bridge you’ll find pontoons to sit on. I enjoyed watching people attempt to sail along the river but really they were just trying not to fall in! Look out for the unusual Hatch Memorial Shell which hosts outdoor concerts during the Summer.

9. Soak up some culture at the Isabella Stewart Gardner Museum

Isabella Stewart Gardner Museum

This an unusual museum was created by its namesake and opened to the public in 1903. Here you will find treasures from all around and the world and priceless works of art. The beautiful open courtyard is a work of art in itself with lush flowers and ornate sculptures. The museum was even subject to an infamous robbery that still has not been solved to this day.

Fancy getting in for free? Visit on your birthday like I did for free entry to the museum! It’s also free for anyone called Isabella!

10. Enjoy drinks with a view at Lookout Rooftop Bar

Sunset at Lookout roof top bar

We started a night out at this classy cocktail bar situated in the SeaPort district. It can be found at the top of the Envoy Hotel. I’m not going to lie, drinks are pricey and you may have to queue (we got there early and had no line!) but the skyline view is worth it!

Boston is the laidback older sister of New York with a historic past. It’s the perfect city if you love culture, sport and history. Cram as much in as you can or take it slowly and really enjoy each activity you choose. One thing’s for sure – you’ll never be bored in this loud and welcoming city!

Cat x


Leave a Reply

Fill in your details below or click an icon to log in:

WordPress.com Logo

You are commenting using your WordPress.com account. Log Out /  Change )

Google photo

You are commenting using your Google account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s