There are so many wicked great things about Boston. The history, the seafood, the accents.
A long weekend in Boston allows you the time to really soak up the city’s history, travel from downtown to nearby historic sites, and try several of the city’s great restaurants.
One thing you should not do while in Boston is call it Beantown. The locals prefer to call it “the Hub.” Writer Oliver Wendell Holmes gets credit for this turn of phrase. (He called the Massachusetts State House “the hub of the solar system” in an article he wrote in 1858.)
During your visit, it may also feel like New Englanders have their very own language. For example, “wicked” is used instead of “really” or “very.” At the end of the article, we included a few unique words or phrases that you should know before your trip. Be sure to check it out!
There are several areas to stay in Boston that work especially well for a weekend trip: the Back Bay, Beacon Hill, West End, and Downtown.
One hotel with an interesting history is The Liberty. It’s located in the Beacon Hill neighborhood along the Charles River. The hotel is a former jail built in 1851, but don’t worry – the last prisoners moved out in 1990. Try to book a room looking out onto the river and away from the lobby area. The atmosphere at the hotel can be lively, but if you aren’t right next to the main area, the rooms are quiet and well-appointed.
The Liberty is next to a T stop, which is the cheapest and fastest way to get around town. The T, which is what Boston’s train/subway system is called, is very user friendly. Boston is also very walkable, and cabs work too as long as it’s not rush hour.
Once you get settled and are ready to eat dinner, walk or cab to the North End. The North End is Boston’s version of Little Italy, and it’s the city’s oldest neighborhood.
I can honestly say that I’ve never had a bad meal at any restaurant in the North End, but Al Dente has become my favorite. A trip to Boston is incomplete without their Shrimp Grand Marnier appetizer and Shrimp and Scallops A La Vodka entree.
That said, if you just walk the streets of the North End and find a restaurant that looks great to you, try it. Some have windows that open onto the street; most post their menus outside so you can peruse their fare and prices. Two tips: there can be significant wait times, especially on the weekends, so put your name in early and find a place nearby to enjoy a glass of wine. Some restaurants do have their own bar area where you can wait as well. Also, be sure to leave room for dessert – but don’t eat it at the restaurant!
Once you’re done with dinner, you’re ready for a treat at Mike’s Pastry on Hanover Street. The lone may be long, but it moves quickly. Once you’re at the front, you’ll be overwhelmed by the army of cannoli and other goodies, but remember you can take something with you! I always get a chocolate covered cannoli, some pistachio macaroons, and rainbow cookies. Don’t judge. You’ll want to buy the entire case too! Just make sure you have cash, or you’ll leave empty-handed.
There are other places to grab a coffee and a snack,if the line is out the door at Mike’s. Modern Pastry is just up Hanover Street towards downtown.
Start your day with breakfast at Flour Bakery and Café. Chef/Owner Joanne Chang won the James Beard Award for Outstanding Baker in 2016 after garnering nominations each of the previous five years. Flour is known for its sticky buns, but they offer other sweet and savory options like scones, cinnamon cream brioche, and egg sandwiches. They can also satisfy your coffee or tea craving. There are several locations, but check out the one on Clarendon Street.
Once you have caffeine and croissant in hand, walk to the Public Garden. Opened in 1837, it was the first public botanical garden in the country. If you read Robert McCloskey’s Make Way for Ducklings as a child, you’ll want to visit the statues of Mrs. Mallard and her eight ducklings here. They’re located near the corner of Beacon and Charles Streets.
As you walk around the Public Garden, you’ll notice the Swan Boats on the lagoon. They’re a Boston tradition since the 1870s, and the same family continues operate the boats today! The Swan Boats only operate from mid-April through mid-September, and cost a few bucks per person to ride.
Once you’ve floated around the lagoon, it’s time to cross the street to the much older Boston Common. The Common is America’s oldest public park, dating from 1634. It’s the place where more than 1000 Redcoats made camp in 1775 before traveling to Lexington and Concord, the first battles of the Revolutionary War. This is where you’ll start your walk along The Freedom Trail. It’s 2.5 miles long and marked with a thick red line. It’s the best way to see the history of Boston and really, of America.
There are 17 official stops along the route, including the cemetery where John Hancock and Paul Revere are buried, the Old North Church, and the USS Constitution. If a 2.5 mile walk sounds like a lot for you or someone you’re traveling with, know that you can stop at any point, and there are places to rest along the way.
One place to rest and eat is Union Oyster House. Located on The Freedom Trail near Faneuil Hall, it’s the oldest restaurant in Boston. In fact, it’s the oldest restaurant in continuous operation in the United States. I would grab a cup of chowder and something from the Oyster Bar. But if you really want lobster, get it here. Then enjoy it against a backdrop rich with American history. These are walls you wish could talk!
Neptune Oyster is another excellent choice for lunch. Located in the North End, they’re known for their shellfish and lobster rolls. You can choose to have your lobster roll either hot with butter or cold with mayo. Or you can try both!
There’s more to see on the Freedom Trail, like Paul Revere’s home and The Old North Church. You know: “One if by land, two if by sea.” And don’t forget Bunker Hill and The USS Constitution. Also known as “Old Ironsides,” it’s the world’s oldest commissioned warship.
You can save some time by taking a cab across the water to Charlestown once you’re done at Copp’s Hill Burying ground. You can also grab the MBTA water shuttle from Long Wharf, near the New England Aquarium.
Bunker Hill is the site of the first major battle of the Revolutionary War. You can climb the 294 stairs to the top of the monument, but after walking The Freedom Trail, you can also just take it in from the ground.
The Charlestown Navy Yard and “Old Ironsides” are the last stop. Naval officers and crew still serve aboard her and lead tours throughout the day. Tours of the ship are free, but you do need a federal or state I.D. or a passport to come aboard.
If the Red Sox are in town, watching a game at Fenway is a bucket list item. If they’re playing your team, even better. Just don’t expect Red Sox fans to welcome you with open arms!
If the team is out of town or it’s the off season, try to work a tour of Fenway into your schedule. It’s the oldest major league ballpark in the country and you’ll be able to sit atop the Green Monster! If the team isn’t in town, tours start at 9 a.m., beginning at the top of every hour, with the last tour leaving at 5 p.m. It takes about an hour. You’ll need to buy tickets for the game or the tour in advance. Tour tickets go on sale 30 days before their date.
If baseball isn’t your thing, check out Community Boating Inc.. You can rent a kayak and spend the evening paddling along the Charles River. Just give yourself enough time to enjoy the scenery, because you’ll need to be back on land thirty minutes before the sun sets.
You can’t make a reservation. It’s strictly first come, first serve. They say they rarely run out, though, and you can rent a single or double kayak for the whole day for $50.
Whatever you do, you want to eat dinner at Island Creek Oyster Bar. Island Creek doesn’t just own the restaurant, they are the oyster farmers. If you really want to see how the oyster makes it to your plate and you have a car, you can book a tour at the Island Creek Oyster farm in Duxbury, about an hour south of Boston.
Island Creek Oyster Bar does take reservations, but only about a month in advance. If you choose to go to the game, the restaurant is near Fenway, so you can walk to the ballpark from there.
The Hawthorne, which is next door to Island Creek Oyster Bar, is an excellent place for a cocktail.
This will be a bit of a choose-your-own-adventure day, starting with breakfast. First option: The Friendly Toast. You can opt for either the Cambridge or Back Bay location. There’s something for EVERYONE on the menu, including a breakfast sandwich made with donuts! They open at 8 a.m. and if you have the No Wait App, you can use it here.
The Beehive is a bit later start, opening for brunch at 9:30 a.m. It’s also a livelier location, known for live music. The type of music varies from day-to-day and week-to-week. It starts at 10 a.m. on Sundays and you can make reservations.
Sunday: Morning & Afternoon
Now it’s time to decide how to spend your day. Four great pairings include: The John F. Kennedy Presidential Library and the Commonwealth Museum; The Museum of Fine Arts and the Isabella Stewart Gardner Museum; or, if you have a car, Lexington and Concord and Minute Man National Historical Park; or Salem and Rockport.
The John F. Kennedy Presidential Library and Museum and the Commonwealth Museum are practically right next to each other, right on the water. The Commonwealth Museum is open Monday through Friday throughout the year, but it’s also open on the weekends from May through October.
The Commonwealth Museum is free and is home to one of the 14 original copies of The Bill of Rights, and an original copy of The Declaration of Independence. The John F. Kennedy Presidential Library and Museum is a fantastic tribute to the life and legacy of America’s 35th President. You can access both museums by taking the T (red line) to the JFK/UMASS stop. A shuttle runs to the Kennedy Presidential Library every 20 minutes.
The Museum of Fine Arts and the Isabella Stewart Gardner Museum are located about a half mile south of Fenway Park. It’s about a six-minute walk between the two. The Museum of Fine Arts is home to works by Rembrandt, Renoir, Monet, and Manet. The museum does offer several one-hour tours every day and they are included in your admission. The Isabella Stewart Gardner Museum has a very interesting history. Everything you see in the museum was part of this famous socialite vision and part of her collection. There are 7,500 paintings, along with thousands of books, sculptures, and rarities.
Both museums charge admission fees, but you’ll get $2 off the admission to the second museum when you show them your ticket from the first. If your name is Isabella, you also get free lifetime admission to the Isabella Stewart Gardner Museum! To get there, take the T (green line E train) to the Museum of Fine Arts stop.
Lexington, Concord, Salem, and Rockport all have that quintessential New England feel. Lexington and Concord, are located between 15 and 20 minutes northwest of Boston and you’ll want to rent a car to get to them. Minute Man National Historical Park stretches between the two towns. Here, you’ll see where the first battles of the American Revolution took place. Concord also has a very interesting literary history. Ralph Waldo Emerson, Henry David Thoreau, Louisa May Alcott, and Nathaniel Hawthorne all called the town home.
If you chose to stay in Boston, you’re going to want to find a place to have a drink. Fortunately, we made a list of the 9 Boston Bars That Mix A Mean Cocktail.
If you want to skip the cocktail and go straight for dinner, try Toro. It’s a tapas restaurant. Even though the plates are small and designed to share, you’ll have a tough time narrowing your choices. One larger item that consistently makes the cut is Paella Valenciana. It will take 30 minutes to make, so you’ll have plenty of time to share several small plates. They do not take reservations, so there could be a bit of a wait depending on when you arrive.
There are too many top-shelf restaurants in Boston. To help you choose, we made a list of our 11 favourite places to eat in Boston.
Here are a few words or phrases that make New Englanders special. It would be wicked cool if you used some during your trip, although your accent may give you away.
Bubbler = Drinking Fountain (pronounced Blubblah), the water fountain is in the park, by the way.
No sir (sah)! = No way! (proper response is Yes sir!)
Grinder = sub sandwich
Quincy = town pronounced Quin-zee
Bang = turn (Bang a U-ie)
Jimmies = sprinkles that go on your ice cream
Frappe = milkshake (pronounced frap)
Packie = liquor store
Pissah = good (think “wicked pissah”)
Dunks = Dunkin’ Donuts (it feels like there’s one on every corner, especially in the suburbs)