Neighborhood Guide: An Afternoon in Charlestown

Nestled on the banks of the Boston Harbor, Charlestown is a vibrant neighborhood where centuries of American history meet modern urban charm. As the oldest neighborhood in Boston, Charlestown is home to iconic landmarks like the Bunker Hill Monument and the USS Constitution, alongside charming brick row houses, cozy pubs, and a thriving waterfront. Here are our recommendations for an afternoon exploring the neighborhood: by Nicole Rosania <a href="https://www.thebostoncalendar.com/events/waverly-kitchen-bar-charlestown/410083">1) Brunch at Waverly Kitchen &amp; Bar</a> Located in the heart of Charlestown, Boston, just steps away from the Bunker Hill Monument and the Freedom Trail, Waverly Charlestown is a neighborhood restaurant that serves breakfast, lunch, and dinner seven days a week. Join us for a legendary brunch, dinner, and cocktails in our cozy dining room, or grab coffee and lunch on the go. 2) See the Zakim Bridge from Pleasant Street Pleasant Street lives up to its name—a peaceful, tree-lined stretch tucked into the heart of Charlestown that captures the neighborhood’s timeless appeal. Lined with classic brick townhouses, historic wooden homes, and the occasional hidden garden, Pleasant Street feels like a walk back in time. You can see the city skyline and the Zakim Bridge from the hill. Plus, the Bunker Hill Monument is just one block away! 3) Shop at Junebug There are many cute boutiques around Charlestown, but Junebug is our favorite! Stop here for gifts, home decor, and floral arrangements. <a href="https://www.thebostoncalendar.com/events/uss-constitution-museum">4) Tour the USS Constitution</a> The USS Constitution, also known as “Old Ironsides,” is the world’s oldest commissioned warship still afloat and a symbol of early American naval power. Docked at the Charlestown Navy Yard, it offers visitors a chance to explore a piece of living history and learn about its legendary role in the War of 1812. <a href="https://www.thebostoncalendar.com/events/1-oysters-at-monument-restaurant-tavern--51">5) Dinner &amp; Drinks at The Monument</a> Cozy neighborhood restaurant perfect for drinks, appetizers, or dinner to cap your afternoon in Charlestown! Plus, The Monument has $1 oyster deals!

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S22: conversations

Wondering what to do in Boston? Places to eat? Free activities? Good for a group? Date night spot? Girls night out? The best things to do? Ask Joyraft!

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S4: top picks

The most fun, cool and unique things to do in Boston. Can’t miss events, shows and experiences. Concerts, restaurants, bars, free things in Boston and beyond.

The most fun and cool events happening around Boston

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S11: happening this weekend

What to do in Boston this weekend? From festivals, concerts, performances, free events, screenings and more, Joyraft has the best things to do in Boston.

25+ things to do in Boston/Cambridge/Somerville this weekend

Things to do in Boston this weekend

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S21: roundups

Our top picks: outdoor dining, free events, spring festivals, best bars, upcoming concerts, museum parties - the latest in and around Boston.  Slug: joyraft-top-picks-best-things-to-do-boston-ma

Top picks of the best things to do in and around Boston

Joyraft picks: Boston’s best things to do

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S17: interest based

Your guide to everything free in and around Boston. From events, to fairs, to festivals, to outdoors. Joyraft has all the free events happening near you.

100+ free things to do in Boston and beyond

Free things to do in Boston

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S28: calendar experiences

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S20: c+d experiences

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S16: editor picks

The most unique and can’t miss things coming up in Boston / Cambridge / Somerville and beyond. Festivals, food, drinks, fairs, concerts, art and free activities.

Unique and Can’t Miss Things to Do in Boston

Can’t-miss things to do in Boston 🚨

Can't-miss things to do 🚨

S2 (A): top experiences

The most popular things to do on Joyraft. Concerts, restaurants, bars, events, parties, openings, kid friendly, date ideas, free things in Boston and beyond.

Top 20 things to do in Boston

Top 20: Joyraft’s most popular

Top 20

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S3 (A): trending experiences

Discover can’t miss events and things to do in Boston. The most fun, unique and cool events coming to the Boston area this spring and summer.

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S19: interest based

Kid-friendly events in Boston

S18: interest based

Where to eat and drink in Boston? Joyraft has Boston’s newest bars, restaurants and specials. Drinks and pre fixe dinner menus. Cambridge & Somerville too.

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Neighborhood Guide: An Afternoon in Charlestown

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