Weekend Getaway to Boston
As the birthplace of the American Revolution, Boston is home to some of the most historically significant sites in the country. And let me tell you, this Massachusetts gem oozes with history. In addition to playing a crucial role in the nation’s past, Boston is known for its many famous dishes (clam chowder anyone?), pre-colonial architecture, loyal Red Sox fans, and that quintessential accent. As the official capital of New England, it’s one of the most iconic cities in the USA, and it has a certain charm despite its big-city status. This travel guide will cover when to visit, where to stay, and all the best things to do on your weekend getaway trip to Boston.
This is your weekend getaway guide to Boston, Massachusetts.
Getting to Boston
Boston Logan Airport is your best option for getting to the city. It’s a large airport with plenty of direct flight options. It’s also a hub for Delta Air Lines as well as a focus city for low-cost airline JetBlue. Another way to reach Boston is via the train route traveling between Boston and Providence, Rhode Island.
Getting Around Boston
Skip the car rental in Boston.
Driving in Boston can be a bit of a nightmare. Instead, I highly recommend walking whenever possible or using the convenient subway system. The underground in Boston is referred to as the “T”, and you can purchase fares right from the kiosks found at the bottom of each station entrance. Download the app Citymapper to help you figure out which subway line and stops to use.
Listen: The Perfect New England Fall Road Trip Playlist
Best Time to Visit Boston
SUMMER
This is a popular time to visit Boston. The weather tends to oscillate between comfortably warm and sunny or miserably hot and humid with the occasional thunderstorm. If you’re seeking out a spot to celebrate the Fourth of July – look no further. Boston has one of the best fireworks shows in the country on Independence Day! Summer is peak tourist season, so expect crowds, traffic, and to pay a premium for lodging.
AUTUMN
There’s just nothing quite like New England in the fall. This is my favorite time to explore Boston! The weather is pleasant, and fall colors throughout New England are the best in the country. Autumn is another peak time for tourists, but a visit in early September before the leaves turn can help you avoid the crowds.
WINTER
Boston experiences cold, windy winters and remarkably heavy snowfall. The severe weather can make it rather unpleasant (or even dangerous) to try to explore the city which deters most tourists. If you happen to visit during a mild part of the season, you’ll be greeted with lower prices and fewer crowds.
SPRING
The spring season in Boston is short but very sweet. Predicting exactly when this period of pleasant weather will hit is a bit of a gamble, but it’ll pay off if you get it right. Spring is a slow tourist season, so this is a great time to visit for lower prices and to beat the crowds.
Where to Stay in Boston
For the most convenient location, look for a place to stay in Beacon Hill or Downtown. To be nearby historical spots and great restaurants, check out the North End. For a slightly quieter neighborhood that’s just a subway stop from the action, Back Bay in Boston’s South End is a great location. Keep in mind that Boston accommodations can get a bit pricey, so be sure to work that into your planning.
The Revolution Hotel
This is where we stayed on our trip as it ticked the boxes of location, style, and affordability (by Boston standards). Although it suited our needs, I will say these rooms were small. Like, laughably small. We opted to get a room with a private bathroom, but the shared bathrooms were almost more convenient (and nicer, actually) than trying to use the one in our tiny room, so consider that when booking. That being said, the bed was comfy, the staff was wonderful, and they offer free loaner bikes!
Things to Do on a Weekend Getaway to Boston
Learn the nation’s history on the Freedom Trail
The Freedom Trail is a must on your first visit to Boston! This iconic path winds its way through the city, connecting 16 nationally signific historic sites. You can walk this path on your own as you meander through Boston, or you can join a guided tour. From the Old South Meeting House where the Boston Tea Party began to the site of the Boston Massacre where Bostonians and Redcoats clashed in the streets, the amount of history is remarkable. If you’re not able to walk the full 2.5-mile path, be sure to plot out a few top spots to check out.
Seek out Acorn Street & Beacon Hill
Nestled in the neighborhood of Beacon Hill is one of the country’s original cobblestone streets. Acorn Street might be the most charming little road in the country. Its cobbled path lined with federal-style row houses, gas-lit street lamps, and climbing ivy will transport you back to colonial Boston. While you’re here, be sure to meander around the rest of the neighborhood as well. This historic district is one of the oldest neighborhoods in the U.S. and is now one of the most expensive and desirable places to live in Boston.
Discover Little Italy in Boston’s North End
Speaking of historic neighborhoods, you absolutely must venture over to Boston’s North End. Amongst the many restaurants and bakeries in this part of town, you’ll find the former home of Paul Revere as well as the Old North Church where Revere himself waited for the famed signal (one if by land, two if by sea). Nowadays, this area is known as Little Italy, and it’s every bit as charming as you might imagine with some of the best Italian establishments in the country. There are too many incredible restaurants to choose from, so just wander along Hanover Street until you smell something you can’t resist.
THE BEST CANNOLI: As you may have guessed, cannolis are a popular treat in Boston. When it’s time for dessert, make a stop at Modern Pastry, which I’m certain serves the best cannoli in the city. Why? Because, unlike other bakeries, Modern Pastry fills their cannolis fresh when you order. No soggy cannolis here!
Sample Boston’s iconic dishes
We’ve already talked about the mouthwatering Italian dishes, but Boston has plenty of other well-known foods you have to try while you’re here. It should come as no surprise that seafood is a big deal around these parts. You’ll find oysters, lobster rolls, and clam chowder a-plenty in Boston (but please, for everyone’s sake, don’t try to be cute and order “chowdah”. I promise, the entire city of Boston is over it). Irish pubs are another Boston classic, so be sure to seek one of these out during your visit. For dessert, there’s the aforementioned cannoli or Boston creme pie.
When looking for your morning cuppa, there’s always Dunkin’, but I’m partial to Tatte Bakery & Cafe. For evening drinks, definitely check out Sam Adams! There’s a great taproom right in the heart of the city if you don’t have time to make your way out to the Sam Adams Brewery on the outskirts of town.
Meander through the Back Bay
This is another beautiful neighborhood to explore and one of my favorite places for a walk in the city. Back Bay is more of a residential area, which means it’s usually a bit quieter and less touristy than other top spots in Boston. Streets like Beacon or Boylston feature picturesque brownstones, and Commonwealth Avenue is lined with green park squares that run all the way through the neighborhood down to the Boston Public Garden. If you’re up for a bit of shopping, head to Newbury where you’ll find high-end boutiques lining the street.
Relax in Boston Public Garden
There’s almost nothing I love more than a morning walk through a city park. The Boston Public Garden is an absolute dream with Victorian gardens, weeping willows, and bridged ponds. In the warmer months, you can even rent a swan boat to paddle around the lagoon.
Wander through Boston’s pre-colonial cemeteries
Call me macabre, but I love a good cemetery. If you’re like me, then you’ll be fascinated by the pre-colonial cemeteries nestled amongst Boston’s high-rises and bustling streets. Kings Chapel Burying Ground is Boston’s oldest cemetery. Don’t miss the Granary Burying Ground which is the burial site of Samuel Adams, John Hancock, Paul Revere, and five victims of the Boston Massacre. Nearby you’ll find Boston’s oldest cemetery, Kings Chapel Burying Ground. Another one worth a stop is Central Burying Ground where many Patriots who died in the Battle of Bunker Hill and the Boston Tea Party were laid to rest.
Stop at the Boston Public Library
The Boston Public Library is absolutely stunning. This place is detailed with intricate ceilings, marbled stairways, gorgeous paintings, and study rooms lined with books that make you wish you had a research assignment. After you’ve fully explored the interior, finish up with a visit to the courtyard where you’ll covered seating and a gorgeous fountain.
Visit Trinity Church
Boston is brimming with architectural beauty, and Trinity Church is a prime example. In fact, this National Historic Landmark is even honored as one of the “Ten Most Significant Buildings in the United States” by the American Institute of Architects. Film-buffs will also appreciate that some scenes from Boondock Saints were filmed here.
Take a train out of the city
Looking to extend that weekend getaway to go beyond Boston? The trains running in and out of Boston each day make for some great day trips! Anyone up for some Hocus Pocus should check out the town of Salem, just 30 minutes away by train. Other great trips include historical Plymouth, seaside Gloucester, or even Providence to discover a bit of Rhode Island. Alternatively, you can skip the train and just take a short ride on the “T” over to Harvard University in Cambridge.
To discover more of New England, take a drive from Boston up the coast of Maine to Portland or Acadia National Park.
Whether you’re a history buff or not, it’s hard not to be captivated by the significance of Boston. With its quintessential New England vibes, cobbled streets, and pre-colonial architecture at almost every turn, it’s easily one of my favorite cities in the country. Whether you’re planning a weekend getaway or a week-long New England adventure, a trip to Boston is just one of those visits that you never forget.
Have any questions about your upcoming trip to Boston that I didn’t answer here? Let me know in the comments!
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