Info Websites

Museum of Fine Arts - First Fridays

www.mfa.org

GreenWay

www.greenway.org

Lawn D
Summer in the City
Boston Harbor Islands
Boston Water Taxi

Activities

Boston Ski and Sports Club

Ski trips from downtown Boston

First Fridays

Dance and mingle the first friday of each month at the Muesuem of Fine Arts

$25
Great Running

Running around Boston 0- Charles River, Boston Common and Castle Island

Free
Roof Tops

Roof top bars and restaurants all around town

https://postunderground.com

Free admission, free food, great live jazz, and veterans-post drink prices are just the means to an end.  The ultimate goal is to enrich the Brookline community by providing a non-capitalist jazz venue open to one and all.

Free

Shopping

Assembly Square - Somerville
Cambridge Side

Boston Living

Social Places & Seasonal Things To Do in Boston

New to Boston? Here’s a locals-first, season-by-season guide to concerts, markets, rooftops, waterfront strolls, cozy winter spots, and more—perfect for weeknights or visiting friends.

Year-Round Social Staples

  • MFA Fridays & ICA: art nights, films, and pop-ups—great for rainy days.
  • The Lawn on D: ring swings, lawn games, and outdoor activations when in season.
  • Harborwalk meet-ups: easy patio hops from Downtown to Seaport.
  • Water shuttles & ferries: turn your commute into a harbor cruise vibe.

Quick Tips

  • Peak times fill fast—grab tickets and restaurant resos early.
  • Transit hack: use the water taxi between Long Wharf & Seaport.
  • Moving soon? Plan early; spring weekends go fast in Boston.
Spring (Mar–May) Fresh Air

Top Picks

  • Harbor Islands (early ferries) and Spectacle Island hikes.
  • SoWa Sundays in the South End: artists, food trucks, vintage.
  • Waterfront walks—golden hour across the Seaport & Greenway.
Summer (Jun–Aug) Free Music

Top Picks

  • Summer in the City at Rowes Wharf—free harborfront concerts.
  • Landmarks Orchestra at the Hatch Shell—picnic on the Esplanade.
  • Seaport rooftops & patios; Lawn on D in full swing.

Rainy-Day Backup

MFA/ICA, bowling or arcade bars in Fenway, cafes in the South End.

Fall (Sep–Nov) Peak Vibes

Top Picks

  • Head of the Charles Regatta—river views near Weeks Footbridge.
  • Late-season SoWa & Greenway leaf-peeping.
  • North End pasta night after a harbor stroll.

Day Trips

Apple-picking, Salem midweek, or a Rockport commuter-rail hop.

Winter (Dec–Feb) Cozy

Top Picks

  • Snowport Holiday Market (Seaport) for lights & gifts.
  • Frog Pond ice skating on the Common (check hours).
  • Heated rooftop igloos—book ahead.

Neighborhood Cheat Sheet

Save these for easy meet-ups and photo-worthy strolls.

New to Boston
Favorite Places, Sites and Social