13 Cheap & Fun Things to Do Solo in Boston This Season [09/27/24]

There’s so much going on in Boston this season, you don’t have to have a pack of friends or a romantic partner to make the most of fall. Take yourself on a date and enjoy one of these 13, low-cost activities that are perfect for a solo day in the city.

by Celina Colby

1) Meet someone new

If you’re feeling bold head to one of Boston’s best bars for single people and chat up a new cutie. Or go for a more casual evening and attend Skip the Small Talk, a night of deep conversation with strangers.

2) Dive into a good book (with a drink)

Whether you want to haunt the halls of Boston’s prettiest libraries, search for a new read at one of the city’s independent bookstores, or sip a cocktail while you read, Boston is a spectacular city to enjoy a good book in.

3) Go wine tasting for free

Many wine shops around Boston do free tastings on a regular basis. Head to Urban Grape in the South End and Vinodivino in Needham to sip and learn about new wines. Get even swankier with a wine and cheese tasting at vomFASS in Coolidge Corner or a shop-and-sip mingle event at Neighborhood Wines in the South End.

4) New England Synth Fest

Musicians and visualizers will team up at the Charles Hayden Planetarium to make it a fully immersive experience in the planetarium dome. Snag a seat and watch this unique performance on the all-encompassing Planetarium screen.

5) Pulpo Day 2023: Stout Festival

Beer lovers pull up a seat at the bar and enjoy Bone Up Brewing’s seasonal brew El Pulpo, a chocolate orange stout aged in whiskey barrels. At this event you can taste the 2023 edition as well as vintages from years past.

6) Leaf peeping around the city

Grab a pumpkin spice latte and take a stroll through Boston admiring the festive colors of the season. We’re mostly talking about leaf peeping but soon, you might spot some holiday lights while you’re at it. You can see lots of foliage right here in the city, but if you have a car consider daytripping to another area of New England as well.

7) Learn a new skill

Taking a class doesn’t have to mean lectures and a reading list. Learn a new language, how to weld your own jewelry, craft a clay mug for your morning coffee, build-a-boob pot in a cheeky pottery class, or knit a cozy, chunky blanket for the cool weather. To find more workshops and courses, filter The Boston Calendar using the “classes” filter.

8) Visit a museum for free!

Get some quality time with Boston’s best pieces of art by visiting The Museum of Fine Arts, the ICA, or the Gardner Museum. The Gardner is free every first Thursday of the month and the ICA is free every Thursday night. The Harvard Art Museums are free every day. You can also get discounted tickets for a regular day by using your Boston Public Library card!

9) Go for a bike ride

Explore a new area of the city by bike! Most neighborhoods have a Bluebikes station and there are some wonderful bikeways for riders who aren’t comfortable on the road. The Somerville Community Path Extension connects Somerville and Downtown Boston.

10) Explore The Innovation Trail

Take a walking tour of The Innovation Trail from Downtown Boston to Central Square and learn about Boston’s scientists, inventors, and entrepreneurs throughout history and today. You’ll be amazed at what’s been invented right here in Greater Boston.

11) Go shopping (locally)

Hunt through vintage finds at Fenway Flea, peruse the local shops at Bow Market (and consider a cocktail at Nook while you’re there), and later in the season shop local for the holidays at the Snowport Holiday Market and SoWa Winter Festival.

12) Watch a movie

Catch a movie at this historic Coolidge Corner Theater, perhaps preceded by a trip to Far Out Ice Cream, or enjoy one of the screenings at the Boston Asian American Film Festival showcasing the Asian American experience in a variety of genres.

13) Grab a latte at a local coffee shop

Grab a book or queue up a podcast and try a new coffee shop on a cozy fall afternoon. Whether you’re waterfront at the ICA Wine + Coffee Bar, snapping an Instagram photo at the ever-chic Faro in Harvard Square, or sampling a waffle sandwich at Ukrainian-owned Esthetic Bean in South Boston, it’ll make for a delicious afternoon.

Photo by @jackdarylphotography

13 Cheap & Fun Things to Do Solo in Boston This Season

Share this event