Weekend Boston Guide: Where to Stay, Eat and Things to Do in Boston

Only a few hours away from many popular cities along the East Coast, Boston is an easy weekend getaway for those looking to explore historical trails and colonial architecture, or those who want to cheer on their favorite sports teams in a sold out stadium. From Beacon Hill to Black Bay, as you set out to explore Boston’s many neighborhoods, I teamed up with Expedia.com to bring you some of the best things to do in Boston as well as where to eat and stay.

Where to stay in Boston

Home to 23 unique neighborhoods, where you stay in Boston depends on what you’re looking for. Black Bay is centrally located and there are many luxury shops and boutiques nearby making it perfect for shopping. The North End is one of the oldest neighborhoods in Boston and it’s home to many of the historic sites found on the Freedom Trail. The South End is a foodie haven with some of the best restaurants in town and Brookline which technically surrounds Boston offers a small town feel.

Regardless of which neighborhood you choose, you really can’t go wrong, as Boston offers a variety of hotel options in any neighborhood.

Things to do in Boston

Brattle Book Shop

Steps away from the Boston Common, a park in downtown Boston, Brattle Book Shop is the oldest used book store in the country. With over 250,000 books, maps and postcards for sale, this family-owned bookstore has been selling rare books and antics since 1825. You can even explore the outdoor, open-air sales lot for the best deals.

Skinny House

Fascinated by narrow houses?

Nicknamed the “Spite House”, Boston’s Skinny House is only 10 feet wide. This four-story private residence has five doors and there is no front door – you can only enter via the small alley at the side of the house.

The story goes that two brothers inherited land around the American Civil War. After the war, when one brother returned, he found out that his brother built a large house taking up most of the property they had inherited. Out of spite he built the Skinny House to purposely block sunlight and ruin his brother’s view.

Although this is a private residence and you can’t go inside, you can walk by and marvel at the skinniest house in Boston by going to 44 Hull Street, Boston, Massachusetts.

Freedom Trail

Stretching 2.5 miles, the Freedom Trail connects 16 historic sites that tell the story of the American Revolution. The sites include museums, churches, burial grounds and more. Although you can certainly do the tour on your own, you can also join walking tours led by 18th-century costumed guides. Some of the unique tours include “African-American Patriots” and “Revolutionary Women.”

Museums

If you want to learn something new or leave feeling inspired, consider visiting a museum during your weekend trip to Boston.

Regarded as one of the best history museums in the city, at the Boston Tea Party Ships & Museum you can walk across restored ships and relive the events of the 1773 Boston Tea Party by joining an interactive colonial town hall. You can also watch a multi-sensory documentary and throw cases of tea overboard. Here you’ll learn about the historic protest that is known as “the single most important event leading up to the American Revolution.”

Another interactive museum in Boston is the Mapparium. Built in 1935, the Mapparium is an inside out stained-glass globe which depicts what the world looked like in 1935. Since a lot has changed since then, many newer countries like Israel and Indonesia aren’t included on the map.

Boston Public Market

For fresh, seasonal produce and seafood, head over to the beloved Boston Public Market.

The Boston Public Market is an indoor year-round market offering delicious treats like hot apple cider doughnuts, freshly baked bread as well as fresh veggies, maple syrups, spices nuts, poultry and dairy.

You can even take a 1-hour free guided tour of the market to learn about the market’s unique history and talk to the makers and artisans, or join a cooking class like the farm-to-table cooking class or the pasta making workshops.

Fun Fact: Boston Public Market is the only “all local” food market in the country. Foods are sourced from 40 New England farmers, fishers and businesses. Everything sold at the market is made in New England.

Helpful Tip: Grab some bagels at Levend Bagelry and enjoy them for breakfast the next day.

Quincy Market

Half food court – half souvenir stalls, Quincy Market is a historic food market which offers plenty of dining and shopping options. From street performers to vendors selling souvenirs and gifts, the Quincy Market is a great place to recharge your batteries while checking out the Freedom Trail.

Offering a variety of food options at a reasonable price, here you can find local specialities, international foods as well as quick bites, sweet treats and snacks at 14 restaurants and 40 food stalls.

Grab a Fenway Frank or a Polish Kielbasa at Dog House, crispy golden french fries at Fisherman’s Net, banana pudding at Magnolia Bakery or clam chowder-filled bread rolls at Boston Chowda Co.

Best Places to Eat in Boston

From delicious brunch spots in San Francisco to food trucks in Nashville, Boston is no different. Boston offers travelers plenty of unforgettable dining experiences from tacos and dumplings to gelato and cannolis.

So where to eat in Boston?

Whether you’re looking for a quick bite to eat or want to explore what the the local food markets have to offer, here are some of the best spots in town where you can eat in Boston, drink and be merry.

Render Coffee

Start your day in Boston by heading over to Render Coffee, a locally owned coffee shop where you can enjoy premium coffee and fresh food in a warm and inviting environment.

On the menu you can find expressos, cappuccinos, lattes, teas and cold brews as well as lox bagels and quiche for breakfast, and salads and wraps for lunch. By the way, the hazelnut latte comes highly recommended and all of Render’s sauces and syrups are homemade.

Masa

Rated one of the top brunch spots in Boston, Masa is a Mexican and Southwest-style Spanish restaurant with a jam packed brunch menu featuring specialty drinks, brunch tapas, “brunch fiesta” and more.

Brunch fiesta is a prix-fixe menu and for less than $10 you can order one first course item which includes fresh seasonal fruit, granola or caramelized plantain empanada. The caramelized plantain empanada comes highly recommend and is served with warm cinnamon Mexican cream cheese. This also comes with either coffee or tea which makes this a good bargain.

Although Masa serves plenty of brunch classics like Bloody Marys’ and mimosas, Masa adds a twist – try speciality drinks like Coconut Mojito, Habanero Watermelon Margaritas and Pomegranate Tequila Sunrise.

Helpful Tip: Since Masa is very popular, reservations are highly recommended.

Roxy’s Grilled Cheese

Last but not least, Roxy’s Grilled Cheese sandwiches, burgers and rosemary truffle fries are a fan favorite. They even have vegan grilled cheese sandwiches, soups and poutine!

Helpful Tip: Don’t forget to check out the hidden arcade and bar in the back.  

How to get to Boston from New York City?

There are plenty of ways to get from New York City to Boston (and any other major city along the East Coast). You can drive, take the bus, train, or fly. However, if you’re looking for the cheapest option, buses are the way to go.

Although there are plenty of bus companies to choose from, MegaBus, BoltBus and Greyhound are the most popular. From New York City, the bus ride takes about 4.5 hours but with traffic, especially on the weekends, expect delays.

A quicker but more expensive option is taking the train to Boston. Amtrak offers comfortable seats, electrical outlets and plenty of storage space for your luggage.

What are your favorite things to do in Boston?