Whatever you want to call it — Beantown, the Cradle of Liberty or just plain ‘ol Boston —this sprawling New England metropolis offers a tantalizing blend of attractions and activities for visitors. Historical sites that played a foundational role in America’s establishment pepper the harbor area, and modern neighborhoods bursting with eclectic storefronts and eateries only begin to scratch the surface of this energetic city. For those who may be passing through or want a condensed itinerary, here’s how to spend 48 hours in Boston, balancing all the facets it has to offer.
Day 1: Scenery & Aesthetics
Boston is one of the oldest cities in America and home to a few key areas that capture glimpses of its humble beginnings. Their architectural style speaks to a distant past and possesses a vibe that screams old New England charm, two traits that make these spaces aesthetically pleasing and worth exploring.
A Journey Through Beacon Hill
Starting off strong in Beacon Hill, travelers first need to fuel up before their adventures can commence. Visitors will notice throughout their time in Boston that cafés like Tatte and Flour are reliable chain options and appear frequently. These casual spots are great for breakfast on-the-go with pastries, sandwiches and coffee, though a more local alternative can be found at Cobblestones: A Beacon Hill Eatery. This cute brunch stop perfectly encapsulates its name, poised elegantly on the pebbled street, and serves everything from sandwiches and salads to wraps, soups and smoothies. The storefront is small and can get busy, but the delicious food makes the experience worthwhile.
Wherever travelers have decided to eat in Beacon Hill, they’ll likely only be a short walk away from one of the most photographed stops in the area: Acorn Street. The picturesque strip of land is a hallmark of the neighborhood, featuring a cobblestone pathway lined by Federal-style row houses. It’s nothing short of adorable, and visitors will know they’ve arrived by all the other tourists snapping their photos in front of the street.
After snapping their Instagram-worthy pictures, travelers can meander over to the nearby Charles Street. The long stretch is Beacon Hill’s main road and is lined with a variety of storefronts and boutiques that make it a great stop for those in search of one-of-a-kind souvenirs. Shops like Beacon Hill Chocolates, Persona Jewelry and Covet, a women’s consignment boutique, offer a glimpse into the goods available along the strip, though an especially noteworthy stop is Beacon Hill Books & Café. The duo-business features an adorable four-story bookstore on the retail side, complete with a winding staircase through the levels, while a quiet café level with the street offers a reprieve from the bustle of Beacon Hill.
Taking in Boston’s Landmarks
Back towards the heart of downtown, a few other attractions convey the city’s history through a different angle. The world-class Boston Public Library is one, and not only is it known for its status as the first free municipal library in the U.S., but it also displays one-of-a-kind architecture. Travelers can head inside and wander through the ornate spaces, stopping in the iconic Bates Hall or perusing through the McKim Courtyard.
Across the street from the iconic library are the equally as significant Boston Common and Public Garden. The Common is the oldest park in America — founded in 1634 — and once served as the meeting place for Puritan communities, housed British troops before the Revolutionary War and was the site for numerous political protests. Similarly, the Public Garden was the first botanical garden in the U.S. The current layout traces back to the Victorians’ preferred style, where the gardener’s art is proudly on display and is evident in the vibrant floral patterns and exotic imported trees seen throughout. While the fall is an especially striking time to visit the area with the colorful trees and cool breeze drifting off the lagoon, the grounds are sure to be beautiful no matter the season.
Bonus: Take Your Thinking Caps Over to Harvard
Still got some steam left after all that exploring? The oldest university in America (aka Harvard) is a quick 15-minute drive from the downtown Boston area. Travelers can join free student-led tours in advance or book a longer visit with the Harvard Visitor Center. A tour map is available for $3 during business hours as well for those who want to take in the historic buildings themselves.
Day 2: History and Local Eats
It may seem like most of Boston’s notable landmarks have been covered on day one, but the city is a gift that keeps on giving! Next on the itinerary is the North End, where visitors can deep-dive into all the nitty-gritty details of America’s past and then recharge at some of the most beloved food stops in the city — history and good eats are a combo Boston does best!
Traveling Back in Time
A 2.5-mile red-brick path taking travelers around to 16 historically significant attractions, the Freedom Trail merits a visit in some capacity, even if it is only to stop and snap a quick photo. Visitors will find sites like the Paul Revere House, the Old North Church and the USS Constitution along the route, and curious minds who want a more immersive experience can purchase tickets for a 90-minute tour online. Otherwise, it’s easy enough to navigate solo and with a little help from Google.
Finish up the explorative day with a trip down the Boston Harborwalk. The 43-mile walkway stretches from the Neponset River in lower Dorchester to Constitution Beach in East Boston, winding around many scenic neighborhoods and attractions. While travelers can choose how far they want to journey, one of the most recognizable sites on the path is the former Griffin Wharf, where the pivotal Boston Tea Party occurred. A commemorative plaque is located along the walkway, also conveniently situated near the Boston Tea Party Ships & Museum for those in search of an additional activity.
Dining on Local Delicacies
Whether visitors go for the good eats or for the historical ties, Faneuil Hall is a bustling marketplace also located on the Freedom Trail. The space was constructed in 1742 and designed to be a prominent meeting place for residents in addition to a central point of commerce for the city. Today, Faneuil Hall and its corresponding branches (North, South and Quincy Markets) are primarily used as indoor shopping centers with storefronts and restaurants. From picking up a teacup-shaped shot glass as a souvenir to dining on lobster rolls and clam chowder at Boston & Maine, Faneuil Hall won’t disappoint.
Once travelers have their fill of perusing the bustling markets, they (naturally) need a sweet treat to complete their meal. And luckily, the famed Mike’s Pastry is only a hop, skip and a jump away. The cash-only bakery was founded in 1946 and rose to fame among locals and visitors alike for their authentic Italian recipes passed down through the generations. Their cannolis and lobster tails are particularly well-loved, though travelers truly can’t go wrong with any of the goodies there.
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