Memories of a Rainy Boston: The City’s Best Umbrella-Sheltered Adventures

1. Christian Science Plaza

The Christian Science Plaza is calming, reflective, and spiritual. Consisting of a huge, mirror-like pool, The Mother Church, and a library detailing the birth of Christian Science, the center boasts beautiful open spaces that allow for peaceful walks in the rain. Attend a concert featuring The Mother Church’s rich pipe organ or explore the history of the Christian Science Publishing House. In 2010, the Plaza underwent revitalizations focused on sustainability and green space expansion, making for an interesting urban ecosystem viewing experience.

2. SoWa Vintage Market

The SoWa Vintage Market encapsulates Boston’s incredible artistic community. Located in the greater SoWa (south of Washington) Art + Design District, SoWa Vintage Market is known for its public art, galleries, shops, and working studios, among other creative venues. The market itself sells unique vintage pieces every Sunday — “rain or shine” — attracting small, local vendors selling everything from crystal glassware to clothing. SoWa hosts a special, open-door celebration in which visitors can meet the artists themselves on the first Friday of every month.

3. Reilly Memorial Rink

Ice skating is a winter staple in Boston, and while the rain might wash away Frog Pond’s icy outdoor rink, those looking to skate can escape from city life for a quiet, weather-protected place to skate — one full of childhood nostalgia of one’s first time skating. Reilly Memorial Rink is one part of the Department of Conservation and Recreation’s seven ice rinks, six of which are indoor and free. Open until mid-April, the arena offers no charge to skaters so long as they bring their own skates. Rentals are for sale, though, and Reilly Rink in particular dedicates time for hockey players of any age with designated rink time.

4. Harvard Museum of Natural History

The Harvard Museum of Natural History offers a fascinating afternoon on Harvard’s Cambridge campus. The exhibitions feature enormous whale bones, precious gemstones, the famous Glass Flowers gallery, and more. On some Thursday nights, the museum hosts special ArtsThursdays celebrations, where visitors have tried edible insects and taken photo booth pictures. The Harvard Museum of Natural History is just one museum in the Harvard Museums of Science & Culture, which also includes the Peabody Museum of Archaeology and Ethnology, Harvard Museum of the Ancient Near East, and the Collection of Historical Scientific Instruments.

5. PKL Boston

PKL B0ston — an indoor pickleball spot with great retro vibes — offers high-end dining from “Chopped” champion Christopher Walker, wall art from Boston local Blind Fox, and many, many pickleball courts. With drop-in court time, drilling workshops, and even trivia nights, this site serves Boston as a popular gathering space late into the night. After all, its founding stemmed from a desire to redefine the social spaces in which people bonded with one another after Covid-19. Pickleball is a social sport that took over Boston by storm, and PKL welcomes both long-term experts and beginners.

6. Puppet Showplace Theater

The first and only year-round puppet theater in New England, Puppet Showplace Theatre welcomes children and adults alike to attend their classes, performances, and workshops that reveal the unexpected intricacies of the practice of puppetry — from how puppets fuel slam puppetry to how marionettes move. A recent show at the theater was “A Slice of Crazy Pie: A Marionette Cabaret,” by Madison J. Cripps, which is, according to their website, a “show that will have you shivering, laughing, and wondering if you had too much to drink.”

7. Museum of Bad Art

Established in 1993, the Museum of Bad Art hosts displays that are humorously refreshing. Its gallery includes a collection of anatomically questionable “Poor Traits,” humorously exaggerated celebrity fan drawings, and a confusing depiction of a Red Sox player mistakenly returning back to home from first base. This light-hearted — yet, at the same time thought-provoking — exhibit provides for a comforting and truly unique forgiveness to viewers’ perception of art.

8. Acorn Street

Beacon Hill’s highly-photographed Acorn Street serves as a testament to the neighborhood’s colonial history. Its beautifully cobblestoned pathways shine particularly after rainstorms, and are home to numerous heartwarming activities: Take walking tours, admire the gaslit streets, and snap Polaroid films of the brick-clad buildings and intimate architecture. Particularly during the Holiday season, the street is lined with festive lights and other jolly decor. Nearby are the iconic State House, Boston Common, and many cozy food stops, such as Somenya and the Paramount.

9. Boxaroo

Located right by the Red Line’s Government Center stop, Boxaroo challenges visitors’ puzzle-solving and team-building skills with a selection of escape room adventures. The immersive experiences offered include solving a magician’s mystery, rescuing lost art for a museum, and discovering a bestselling author’s secret. Each adventure is well-designed, organic, and ranges from moderately to extremely challenging in difficulty, therefore attracting even expert puzzle solvers. In 2021, Boxaroo was voted number 2 for USA Today's Top 10 Escape Rooms in 2021.

10. Custom House Tower Observation Deck

Visit the Custom House Tower Observation Deck and admire the beauty of Boston through a quintessential feature of the city. This iconic structure overlooks the Greenway, Boston City Hall, Boston Harbor, and many more famous sites. Its Greek-revival-inspired architecture — including the beautiful, iconic dome — is rich with history. Since 1997, the tower has been home to a Marriott timeshare hotel, in which guests can enjoy the spectacular view of nighttime Boston.