Things To Do

History

Freedom Trail

A 2.5‑mile self-guided walk linking 16 key Revolutionary sites—Boston Common, Paul Revere House, Bunker Hill Monument—and a perfect intro to Colonial history. There are also plenty of guided tours available in this area.

Boston Common & Public Garden

America’s oldest city park (1634) and its adjacent Victorian-era Public Garden (1837). Ideal for swan‑boat rides, picnics, and people-watching in the heart of the city.

Day Trip to Salem

Just a 45-minute drive or commuter rail ride from Boston, Salem is a must-see for history buffs, spooky story lovers, and fans of quaint coastal towns. Best known for the infamous 1692 witch trials, Salem offers a mix of colonial history, maritime heritage, and modern witchy flair.

Day Trip to Lexington and Concord

Step into the pages of history with a day trip to the charming towns of Lexington and Concord, located about 30 minutes from Boston. These towns mark the very start of the American Revolutionary War and offer a mix of historical landmarks, scenic trails, and small-town New England charm.

Culture & Sports

Isabella Stewart Gardner Museum

Intimate museum housed in a Venetian-style palace with lush courtyard and unique installation-style exhibits. Also the site of a famous art heist - you can still see empty frames on the walls where the stolen pictures once hung.

Museum of Fine Arts

Discover nearly half a million artworks spanning ancient Egypt to Impressionist masterpieces—seasonal exhibits and a stunning neoclassical setting.

Fenway Park

Tour the iconic “Green Monster,” soak up Red Sox history, or catch a game—arguably America’s most beloved ballpark, and right in our neighborhood!

Boston Public Library

Step into America’s first large free public library, a true "palace for the people." Explore the historic McKim Building with its murals, grand reading room, and courtyard, or visit the modern wing for books, a café, and creative spaces. Don’t miss free tours, talks, and summer courtyard concerts.

American Reportory Theater

Located in the heart of Harvard Square, A.R.T. is one of the nation’s most celebrated regional theaters, known for bold new works and Broadway-bound productions. Past hits include Waitress, Jagged Little Pill, and The Great Comet. Whether you’re a theater lover or just looking for a memorable night out, A.R.T. offers a dynamic cultural experience in an intimate, world-class venue. Danielle has a season subscription at A.R.T.

The Bebop

This is the bar where Danielle proposed to Matt! The have live music every night of the week, including open mic nights on Thursdays like the one where Danielle serenaded Matt.

Nature

Charles River Esplanade (The Esplanade)

An iconic 3-mile park along the Charles River in Back Bay—perfect for runners, cyclists, picnickers, and anyone seeking a scenic escape. Enjoy public concerts, year-round trails, playgrounds, floating docks, and public boating via Community Boating Inc. Matt serves on the board of the Esplanade Association that helps keep the park beautiful and accessible to everyone.

Whale‑Watching Cruise

Various companies in and around Boston offer seasonal whale watching trips beginning in May.

Borderland State Park

The park where Matt proposed to Danielle! If you have a car and are looking to get out of the city, you can find lovely hiking and biking trails or take a tour of the Ames Mansion and catch a glimpse of the library where Matt popped the question

Food & Drink

Tree House Brewing Company

Located about an hour from Boston in Charlton, MA, Tree House Brewing is a must-visit for beer lovers. Known nationally for its hazy IPAs and meticulously crafted stouts, Tree House offers a beautiful hilltop taproom experience with stunning views, wide lawns, and a laid-back vibe with seasonal food trucks. If you prefer not to travel as far, check out their outpost in the Prudential Center in Boston!

Trillium Brewing

Just steps from Fenway Park at 401 Park Drive, Trillium Fenway is a bright, greenhouse‑inspired taproom offering local craft beers in a beautiful indoor–outdoor space. It is also only steps away from Time Out Market where you can get a wide variety of snacks to go with your drink.

Downeast Cider

Located in East Boston’s shipyard, Downeast Cider serves up unfiltered, locally made cider in a casual taproom with views of the harbor. Try a flight indoors or relax in the seasonal outdoor garden with live music and skyline views. It’s bring-your-own-food, and full of laid-back charm.