Boston Like a Local: A Weekend in The Historic City

Updated On: April 22, 2024 by   Ciaran Connolly

Boston, Massachusetts, a city known for its heritage, deep colonial roots, and history. It’s also home to phenomenal sports, food, and attractions. Boston is also known for its deep Irish roots and because of this, the city is scattered with Irish pubs and traditional music. Boston has much to offer for a weekend away. Whether you’re there for the sports, the history or the shopping, Boston has got you covered. 

With so much to do, places to see, and restaurants to try, it can be hard to decide how to structure your weekend in Boston. Luckily, we have provided the perfect itinerary for you. Hitting all of the fan favourites and the local spots, here are just some of the best attractions for your trip for a weekend in Boston.

Friday In Boston 

Head into Boston on Friday and drop your bags at one of Boston’s many gorgeous hotels. The Seaport hotel offers all the modern amenities of a 4 star hotel with amazing views of Boston Harbor. The hotel is located in downtown Boston and within walking distance of great restaurants, attractions, and museums. 

After you settle into the luxurious rooms, head out for some dinner at one of Boston’s renowned restaurants. Boston, and the surrounding New England area, is known for its seafood and more specifically – the lobster roll. Neptune Oyster serves one of the best lobster rolls in all of Boston. Visitors on Tripadvisor rave about the lobster roll here saying it is the “best I’ve ever had”. With reviews like that it is hard not to give it a try. Whether with butter or mayo, a lobster roll is an irresistible Boston staple. 

Once you’ve finished with a splendid seafood dinner, spend the rest of the evening relaxing at the hotel bar which has both indoor and outdoor seating, heaters to keep out the chill and sits right overlooking the harbor. Watch the sunset and enjoy some cocktails or a local craft brew. 

Saturday In Boston

Boston is a city that breathes life all year round. However, the harsh winters and piles of snow do not always suit walking the Freedom Trail or catching a game at Fenway Park. For that, we suggest the warm temperatures of late spring or summer time to get the most out of Boston. 

Start your Saturday morning by stopping at the Seaport Cafe, located just within your hotel. Grab a patisserie and an iced drink for your stroll along the Freedom Trail. The trail is 2.5 miles long and runs through the historic streets of Boston. Paved in brick, the trail tells the story of the Revolutionary War and the start of America. The trail stops at historic monuments throughout Boston, from the sight of the Boston Tea Party to the Park Street Church. You can walk this trail on your own accord or hire a guide to give you more insight into the history of the city.

Later in the day, consider grabbing tickets and heading to a game at Fenway Park. Fenway is one of Boston’s prized possessions. One of the oldest stadiums in the country, Fenway is more than just a baseball stadium – it is a ritual, a meeting place. Red Sox fans are known for their loud team spirit and their rendition of ‘Sweet Caroline’ during the 7th inning stretch. Whether just a fan for the day or a die hard baseball fanatic, Fenway Park is a must for any tourist in Boston. 

Finish off the evening with entering one of Boston’s Irish pubs. Located just across the street from Fenway Park is Lansdowne Pub, a great spot to enjoy the victory of the Red Sox! Lansdowne is not only a Red Sox sports bar but it has an incredible interior, which propels you back to Ireland the moment you walk through the doors. Did we mention the food at Lansdowne? All of the Irish classics with an American twist. Try the fish and chips, or the Irish burger with a sweet potato bun. Lansdowne is a delectable way to finish your Saturday in Boston. 

Sunday In Boston

Wake up Sunday morning overlooking the sunny bay, but quickly remember you’re still in Boston and there is still plenty to do! Boston, unlike many major US cities, is very walkable. Head over to Quincy Market to get a real New England feel. Built in the early 1800’s, Quincy Market was created for the current Mayor of Boston. Before Quincy Market, there were just wooden shacks lining the outside of Josiah Quincy’s office. In a bid to create a better view, Quincy had the market building constructed. The large building resembled that of Greek architecture. It is two floors, and has shops for just about everything you can imagine. Some of the best fresh seafood the world has to offer, Boston souvenirs, and impeccable seafood chowder make Quincy Market a great morning walk. 

After walking through the market and picking out goodies, take a stroll around the surrounding shops. The area surrounding Quincy Market is all pedestrian friendly, allowing for families, friends, and couples to meander into the various shops. They range from chain stores such as Urban Outfitters, to locally owned shops. If you stick around the area for long enough, you might be able to see a live street performance. The square surrounding Quincy Market is often frequented by college students from Berklee College of Music, showing off their talents. 

You could easily spend all day at the market, however, Boston has one more magical attraction – whale watching! Boston is known for some of its great wildlife, and paired with the New England Aquarium is whale watching. Head on over to Boston Harbor Cruises and grab your tickets for an afternoon of whale watching. During the summer months, humpback and blue whales can be seen by the boat, along with dolphins and seals! If whale watching is a bit too extreme, there is also a lobster catching boat that allows for you to go out and catch your own dinner! 

After a busy day of yummy food, shopping, and interacting with wildlife, finish your trip off by heading into South End Boston. A gorgeous setting of Boston and great restaurants, have your last meal at B&G Oysters. Ultimately known for their delicious oysters, B&G also has a diverse menu of seafood, and pub favorites. 

Getting ready to leave Boston after a loaded weekend like this, it may be hard to leave. There’s a reason people move here and never move back. Between the history of the city, the sport fanatics, and the great history and views of the harbor, Boston is a pretty unique place. This significant city located on the New England shores, is the perfect weekend trip.