It’s a terrible feeling, knowing that in a few short months Boston will become the cold, frigid image of a New England winter. It makes outdoor exploring and walking around miserable, and sometimes almost impossible. But throughout September, October, and even parts of November, Boston weather hits a sweet spot of temperature where it’s nice enough to be outside without being too cold or too hot. During these months, I love to take little outings on the weekend with friends to wander around different neighborhoods and areas of Boston. We can go shopping, get food, and maybe even catch a movie. But where should you go? What’s there to do? And how do you get there? Here are some neighborhoods I love to go to, the shops I visit, and the way I get there.
Union Square
Union Square in Somerville is great for dining and shopping with friends on a weekend afternoon. Check out Ricky’s Flower Market and get some cute plants for your dorm, find some unique vintage pieces at Memory Hole Vintage, and get ice cream from Gracie’s Ice Cream (I recommend the Ube ice cream).
Take the 47 bus towards Central Square 9 stops from Park Drive @ Mountfort St to Green St @ Magazine St. Transfer to the 91 bus towards Sullivan and get off at Somerville Ave @ Prospect Ave (10 stops), which drops you right down the street from Union Square.
SoWa Open Market
Located in the South End, the SoWa Open Market is a market that features art, food, and shopping every Sunday from 10am-4pm, May-October. There are multiple food trucks, art stands, and live music and lawn games! Admission to the market is free to all and a great place to explore with friends!
Take the Green Line inbound to Copley, then walk about 20 minutes to 530 Harrison Ave.
Central Square
Located in Cambridge, Central Square is home to a bunch of fun restaurants for you and your friends! Take your vegetarian friends to Veggie Galaxy for a classic diner with a veggie twist, then to Toscanini’s for dessert. If you’re looking for something to do, head to the MIT Museum to check out their exhibits on science, art, technology, photography and more (admission is only $4 for students!), walk through the Graffiti Alley, or browse the stacks at Cheapo Records.
Take the Green Line inbound to Park Street, then transfer to the Red Line towards Alewife and get off at Central.
Coolidge Corner
Coolidge Corner is a great place to shop, eat, and have some fun! Get sushi at Genki Ya or crepes at The Paris Creperie, browse the stacks at Brookline Booksmith, and catch a midnight movie at the Coolidge Corner Theatre! The Coolidge Corner Theatre runs different series like Science on Screen, where they bring in local professors to give a talk after a showing, and Coolidge After Midnight, where they do midnight showings of movies like The Room and The Rocky Horror Picture Show, as well as a Halloween movie marathon in October.
Take the Green Line C outbound towards Cleveland Circle from St. Mary’s Street (in South Campus) and get off at Coolidge Corner.
Harvard Square
Harvard Square is a great place to eat with friends and spend an evening exploring. Grab some cereal milk ice cream from Milk Bar or a pastry from Flour Bakery and Café, or catch a movie at the Brattle theatre! Harvard Square also has a lot of great places to go shopping (or window shopping).
Take the Green Line inbound to Park Street, then transfer to the Red Line towards Alewife and get off at Harvard.
Davis Square
Somerville’s Davis Square is home to many cute restaurants and stores! Grab some reimagined comfort food from Rosebud American Kitchen and Bar, or grab some pizza and try out candlepin bowling with friends at Flatbread Company inside Sacco’s Bowl Heaven (lane rental is $30/hour, so split the cost and bring your own team!). If you’re looking to spruce up your room (or find a unique birthday gift for a friend), check out Magpie, which has trinkets and art from local and regional artists. Davis Square is also home to Buffalo Exchange, a popular thrift store.
Take the Green Line inbound to Park Street and transfer to the Red Line. Take the Red Line towards Alewife and get off at Davis.
North End
Known as a mecca for Italian food and cafes in Boston, the North End is also the heart of the historic Freedom trail. Indulge in your touristy side and visit the Paul Revere house, then get a cannoli from Mike’s Pastry on Hanover Street. If you’re willing to wait, get in line at Regina Pizzeria, touted as Boston’s original pizzeria.
Take the Green Line inbound to Copley, then transfer to a Green Line train towards Lechmere. Get off at Haymarket.
Newbury Street
Newbury Street is chock full of fun cafes and shops to peruse, like MUJI, a Japanese store featuring stationary, clothing, and household goods. Take a seat at Trident Booksellers and Café and enjoy a coffee and some lunch before browsing the stacks. If you’re into Harry Potter, check out The Fairy Shoppe, a small (like, really small) book and trinket shop specializing in magical and mythical items, as well as a large amount of Harry Potter merchandise.
Take the Green Line inbound to Hynes Convention Center. Or, walk East on Commonwealth Avenue, which becomes Granby Street. Turn right onto Charlesgate, then continue on to Newbury Street.
Downtown Crossing
Downtown Crossing is a great place to go if you’re looking to go shopping. Located close to multiple T stations, Downtown crossing is home to stores like Primark, Macy’s, Old Navy, and more. Street Performers often set up in the streets and play to crowds as they walk by. Downtown Crossing is also within walking distance of Chinatown and the North End, which offer great places to eat after a long day of shopping.
Take the Green Line inbound and get off at Park Street.
Seaport
Boston’s Seaport is home to a myriad of restaurants, shops, and destinations, including museums like the Boston Children’s Museum and the Institute of Contemporary Art. It also houses The Current, a space that holds pop-up establishments throughout the year. Check out the Glossier (a mainly online skincare and makeup brand) pop up from now through October 4th, 11am-7pm.
Take the Green Line inbound to Park Street and transfer to the Red Line. Take the Red Line towards Ashmont or Braintree and get off at South Station. Transfer to the bus terminal and take the Silver Line 1, 1/2, 3, or 4 to World Trade Center.
There are a ton of fun places around the city to explore and experience, so long as you’re willing to go out and find them. So load up your Charlie Card, lace up your walking shoes and get out there!
Great article! Thanks so much for including a meal at Veggie Galaxy in your Central Square, Cambridge recommendations. We definitely welcome non-vegetarians here too.