Things To Do In Roslindale

Explore the "streetcar suburb" of Roslindale to experience the suburban flavor of the city.

Roslindale is primarily a residential neighborhood which earned the nickname "street car suburb" in the early 20th century when Boston began constructing trolley lines to access areas far from downtown. Today, many of these trolley lines are gone, but the residential, treelined streets and localized town centers remain. Stop by the Bay State Model Railroad Museum on South Street to see realistic miniature models of Massachusetts towns when trolley cars crept their way through commercial centers.

Over the years, Roslindale has become a thriving food shopping destination with diverse specialty stores, such as Tony's Market which specializes in authentic Italian ingredients, and numerous popular dining destinations. 

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Top Activities in Roslindale

Arnold Arboretum: Take a walk down Fairview or Mendum Street to one of the quieter gates or walk up to the Walter Street Gate where you can take a serene nature walk, relax, or discover the thousands of plant species in the Arboretum.

Boston Public Library - Roslindale Branch: Visit the Boston Public Library Roslindale branch and explore its early 60’s architecture, enjoy a good read, or attend one of their events. 

ComedySportz Boston: Enjoy hilarious live entertainment as two teams compete, improvising scenes, games, and songs on the spot, inspired by the TV show Whose Line Is It Anyway. 

Distraction Brewing Company: Visit Distraction Brewing Company’s taproom and beer garden located in Roslindale Village and enjoy quality craft beer, take a brewery tour, or attend one of their upcoming events. 

Roslindale Village - Main Street: Recognized as the original Main Street district, Roslindale Village Main Street is a thriving commercial hub filled with vibrant unique shops and bistros. There you’ll have the opportunity to participate in many events and programs throughout the year such as their Summer and Winter Farmer’s Market, Caribbean Food Festival, outdoor movie nights and more (typically located in Adam’s Park).

Russian Orthodox Church of the Holy Epiphany: Visit the Russian Orthodox Church, just a short walk from Roslindale Village and marvel at its distinctive architecture, characterized as medieval Russian Novgorod/Pskov style.

The Bay State Model Railroad Museum: The Bay State Model Railroad Museum features model railroads that showcase what old Massachusetts towns were like during the 19th century trolley era. 

The Square Root: Discover the Square Root Café, where coffee meets craft beer and wine. Enjoy lively karaoke nights and live music performances, or attend one of the music, comedy, and social events that regularly take the stage.

The Substation: The Substation offers Roslindale and nearby residents a vibrant coworking space by day and events, performances, and a full bar by night.

Where to Eat in Roslindale

753 South: 753 South Restaurant and Bar offers modern American fare in a welcoming atmosphere that provides live music and outdoor dining. 

Delfino Restaurant: Delfino is a charming Italian restaurant, offering delectable classics and an extensive selection of wines.

Guira & Tambura: Visit Guira & Tambura and indulge in delicious Caribbean flavors from the Dominican Republic.

Shaking Seafood: Satisfy all your seafood cravings at Shaking Seafood, a New Orleans-style restaurant bursting with delightful flavors.

The Pleasant Cafe: The Pleasant Cafe, standing for over 80 years, offers a nostalgic experience with its old-school diner ambiance and is most famous for their hand-crafted, Italian-style pizza.