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Friends Having Breakfast

Fab4 Local Recommendations | Charlestown

By 4Squares Residential Group with Judi 411


Next on our tour: Charlestown, the oldest part of Boston—established even before the city itself! This historic gem, nestled between the Charles and Mystic Rivers, is packed with charm and things to do and has also been the backdrop for iconic films like The Town, Good Will Hunting, The Departed, and Mystic River. Charlestown offers something for everyone, from cozy cafés and top-tier restaurants to fun museums and local hangouts. Wander the cobblestone streets, admire the historic homes, or take in the view from the Bunker Hill Monument—Charlestown blends history, stunning architecture, and cinematic allure perfectly!


Enjoy History and Art

Charlestown is full of must-see spots, but no visit is complete without a stop at the Navy Yard. You can even walk there from downtown Boston via the Freedom Trail, adding a historic touch to your journey before exploring this iconic landmark.


Established as one of the nation's first six naval shipyards, the Charlestown Navy Yard was a center of innovation, providing jobs for skilled workers and housing officers, sailors, and Marines for 174 years. Today, visitors can explore two historic warships, two museums, and various artifacts and buildings, offering a fascinating journey through the past, present, and future of the U.S. Navy.


The U.S.S. Constitution Museum offers a deep dive into the history of America’s oldest commissioned warship, known as "Old Ironsides." Through engaging exhibits and hands-on activities, visitors can explore the ship’s storied past and the lives of the sailors who served aboard. 


Looking for a fun twist and a way to entertain the little set? Try the Constitution Mini-Golf, a family-friendly course designed around naval history. Plus, don’t miss Sensory Friendly Sundays, held from 9-10 am on select Sundays through December, offering a quiet and welcoming experience for visitors of all ages with sensory sensitivities.


If you’ve had your fill of history and are looking for something different, The Artists' Group of Charlestown is a vibrant community of local artists dedicated to fostering creativity and collaboration. Housed in the historic StoveFactory Studios, the group offers exhibitions, workshops, and open studio events that showcase a wide range of artistic talent. With a mission to inspire and engage artists and the public, the Artists' Group plays a vital role in Charlestown’s cultural landscape, making art accessible to all.



Eat All Three Meals

Situated in the vibrant Hood Park neighborhood, just beyond Sullivan Square, Tradesman is a standout spot inspired by the area’s hardworking, blue-collar roots. The name pays homage to the craftsmen and laborers who built the community. By day, it’s a cozy coffee shop serving artisan brews and pastries—don’t miss their mini-donuts! As evening falls, Tradesman transforms into a lively dining destination with a full menu featuring delicious pizzas, burgers, craft cocktails, and more, making it a favorite for great food in a relaxed setting. 


Located in the heart of Charlestown, just steps from the Bunker Hill Monument and the Freedom Trail, Waverly Kitchen and Bar is a Boston Magazine 2024 Brunch Favorite. This neighborhood gem serves breakfast, lunch, and dinner seven days a week, offering a cozy dining room perfect for enjoying a legendary brunch— their pancakes are second to none!— or evening cocktails. Whether you’re in the mood for a leisurely meal or a quick coffee and lunch on the go, Waverly Kitchen is the ideal spot to savor scrumptious food in a warm, welcoming atmosphere.


Play (or, in this case, Bowl) and Hear Great Tunes

Urban Wild, just a few doors down from Tradesman in Charlestown, is a buzzing hotspot that fuses urban chic with rustic charm. This lively venue boasts a fun-filled bowling alley and a mouthwatering menu of locally sourced dishes and craft beverages. Known for its high-energy events, Urban Wild lights up with Throwback Thursdays and Country Saturdays, featuring local musicians and endless entertainment. Don’t miss out on any of the action—check out their event calendar for the latest updates and get ready for an unforgettable time!


Meet Friends (or Make New Ones) Over Libations

The Warren Tavern in Charlestown is a quintessential Charlestown experience, steeped in history and tradition since 1780. Located steps from the Freedom Trail, this iconic tavern exudes a warm, inviting atmosphere where you can savor classic American fare and a diverse selection of craft beers. With its rich legacy, friendly service, and hearty menu, the Warren Tavern offers an authentic taste of Charlestown's past and present, making it a must-visit for history buffs and anyone seeking a cozy spot to unwind and enjoy anything from a few drinks to a hearty meal.



If you’re on a mission to hit every Irish bar in town, the Tavern at the End of the World is one you can’t miss. This gem offers a perfect escape from the hustle and bustle of city life, all while being right in the heart of it. With its cozy, authentic Irish pub atmosphere, signature culinary fare, and extensive beer selection, it’s a haven where you can relax, unwind, and enjoy a genuine taste of Ireland. Whether you’re seeking a break from the daily grind or simply looking for great company and a vibrant setting, the Tavern at the End of the World is your go-to retreat.


At 4Squares Residential Group, we’re all about celebrating the Medford lifestyle and making every day a reason to love where you live! Follow us for more hot tips on hidden gems and fun activities hiding in plain sight. Or stay in the loop by subscribing to our email newsletter today, and never miss out on all the places to see and be seen!

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