We try not to play favorites, but it’s hard not to name Boston as one of our favorite cities. The New England destination is packed with history, culture, and charm, offering endless things to explore. Whether you’re a food enthusiast, history buff, nature lover, or anything else, Boston has something for everyone to enjoy. The waterfront city has seen centuries of milestones and history, with many of those moments captured in the streets and buildings. Whether you’re visiting Boston for the first time or returning for the hundredth, here are twelve things everyone should do at least once.

*View of downtown Boston and fountains along the Rose Kennedy Greenway*

Boston Public Market

Who doesn’t love a year-round market? The Boston Public Market is an indoor marketplace featuring dozens of local artisans and food producers from New England. From fresh produce to crafts, the marketplace is versatile and lively – the ideal place to meander and do a little shopping. The market regularly hosts cooking demonstrations, tasting events, and kid-friendly activities, most of which are free! Union Square Donuts is a must-visit and has some of the best donuts you will ever try.

Fenway Park

Regardless of whether or not you’re a baseball fan, Fenway Park is a destination worthy of visiting. The home of the Boston Red Sox, it’s the oldest active ballpark in the Major League, dating back to 1912. See a baseball game, or simply hop on a tour. Available year-round, standard public tours explore the historic grounds with a 60-minute guided tour featuring team, ballpark, and player history. The ballpark additionally hosts a few more specialty tours, including an 8 AM Field Level Tour offering a unique experience for early risers, “Fenway in Fifteen” when you want to see the ballpark but don’t have a full hour to spare, and Pregame Tours during baseball season for access to the field’s warning track, a visit to the oldest seats, and more (source).

*Street corner of Chestnut & Charles Streets in Beacon Hill*

Freedom Trail

The Freedom Trail is a convenient group of historical sites that spans over a 2.5-mile route. It features sixteen sites that history lovers will admire while visiting Boston. The Freedom Trail makes it easy to check off multiple sites in one morning or afternoon. The flexibility to choose what you visit and when is certainly a perk if you’re short on time, but if you can spare a few hours, try a guided walking tour. Stops on the trail include the Boston Common, Park Street Church, Granary Burying Ground, King’s Chapel & Burying Ground, Benjamin Franklin Statue & Boston Latin School, Old Corner Book Store, Site of Boston Massacre, Paul Revere House, Old North Church, Copp’s Hill Burying Ground, Bunker Hill Monument, and USS Constitution.

John F. Kennedy Presidential Library and Museum

Located a bit off the beaten path, the JFK Museum is a great rainy-day excursion. Dedicated to the memory of President John F. Kennedy, the library has breathtaking views of Boston’s waterfront. The experience begins with a short film documenting JFK’s life up to his first presidential campaign. The exhibits feature an in-depth look at the campaign process and the subsequent win. You’ll learn about life with his family and what it was like living inside the White House. Dive into significant moments like the Cuban Missile Crisis, the establishment of the Peace Corps, and the space program. Additional exhibits include Robert Kennedy’s time serving as Attorney General, Jacqueline Kennedy Onassis’ work advocating for the arts and historic preservation while serving as First Lady, a collection of fashion from her time in the White House, a special Ernest Hemingway Collection, and more.

Photo Shoot at Acorn Street

Originally a lane used by service people to access the homes of wealthy families, Acorn Street is now considered the most photographed street in America. The uneven cobblestones and old-school lamps among historic row houses have preserved the neighborhood’s original charm, taking visitors back in time to the early 19th century. Tucked away in Beacon Hill, Acorn Street is just as residential today as it was in 1820, but you’ll often find a smattering of tourists and photographers lingering with the hope of capturing the perfectly aesthetic photo.

Pop Culture Cold: From Cheers to Good Will Hunting

Boston has been an epicenter for pop culture references for years. With many artists and celebrities hailing from the New England city, it has served as a source of inspiration for many shows and films. Head to the Back Bay to visit the Cheers Bar - originally Bull & Finch Pub - on Beacon Street, the famous inspiration for the sitcom starring Ted Danson. L Street Tavern is the famous dive bar from Good Will Hunting and still promises a good time among friends. You can also sit on the same park bench as Robin Williams in Good Will Hunting in the Boston Common. The Buttery in the South End was featured in the movie Spotlight, starring Rachel McAdams and Mark Ruffalo. You could also hop across the river to Harvard Square, which was featured in Legally Blonde and Gilmore Girls.

Rewind the Clock by Visiting the Mapparium

A unique interactive historical experience, The Mapparium in the Mary Baker Eddy Library offers an inside look at the planet as it was in 1935. A three-story, walk-through, stained-glass globe shows a map of the world from over nine decades ago from the inside out. It’s a masterpiece and one of the more distinctive experiences in Boston, offering a show that uses LEDs to highlight the historical borders of the time.

Step Outside for Urban Greenspaces

Boston has many beautiful green spaces throughout the city. You could say the Boston Common is the original green space, as America’s oldest park. Founded in 1634, the Boston Common has a long history, from serving as a home to British soldiers during the Revolutionary War to acting as the epicenter of independence celebrations. Today, the 50-acre park is a place for gathering and peaceful respite with playgrounds, a frog pond, baseball fields, and more. More recently, the Esplanade was developed along the Charles River in 2001, between downtown Boston and Cambridge. It’s become one of the city’s favorite parks, with 17 miles of landscaped paths, an outdoor concert venue, playgrounds, recreational activities like kayaking, waterfront gardens, monuments, and more. The Rose Kennedy Greenway is a 1.5-mile modern park with gardens, promenades, fountains, and more, with a regular schedule of events. Finally, head to Castle Island in Southie for underground caves and woodlands, native to the geographic region.

Stroll Down Famous Streets

There are several famous streets throughout Boston, each with a unique history and role. The historic Beacon Street is one of Boston’s main roads, running over 10 miles through the heart of the city, and is famously home to mansions overlooking the Boston Common. Newbury Street in the Back Bay is known for shopping and dining, with eight blocks of designer boutiques, small local businesses such as coffee shops, art galleries, and retail stores, outdoor cafes, and more. Boylston Street is home to Copley Square, Trinity Church, the Boston Public Library, and many great restaurants and shops. Commonwealth Avenue is famous for a greenway in the center featuring memorials and statues such as the Boston Women’s Memorial and Alexander Hamilton. Despite being in the center of a busy road, it’s a beautiful, surprisingly peaceful path, with benches scattered throughout and brownstones lining either side. Finally, Charles Street in Beacon Hill features brick-lined sidewalks filled with antique shops, restaurants, and plenty of character.

Tour the Massachusetts State House

An architectural treasure from the Revolutionary period, the Massachusetts State House is one of the oldest buildings in Boston. Designed by Charles Bulfinch, Samuel Adams laid the cornerstone in 1795 before the building was completed in 1798, and Paul Revere covered the dome in copper in 1802. Statues memorializing historic figures are on display throughout the grounds, including those of John F. Kennedy and Mary Dyer. One of the building’s main features is the Grand Staircase, featuring stained-glass windows, historic seals, and murals. The Massachusetts State House is a part of the Freedom Trail, and free tours are offered on weekdays.

Treats in Boston’s “Little Italy”

Known as “Little Italy”, the North End is Boston’s oldest residential neighborhood. The area became a hub for immigrants in the late 19th century, predominantly Italian, as evidenced by the many restaurants and bakeries that fill the area. Make sure to have plenty of cash on hand to visit iconic spots like Mike’s Pastry and Modern Pastry for made-to-order cannoli, and Galleria Umberto for Sicilian-style pizza. For something a little more formal, Neptune Oyster Bar is a must-visit if you love seafood.

Walk Through Faneuil Hall

Four historic markets make up Faneuil Marketplace: Faneuil Hall, Quincy Market, North Market, and South Market. The promenade features cobblestone pedestrian roads plus live music and entertainment year-round. Faneuil Hall has long been known as Boston’s central meeting space. Meetings and discussions have been held here around many historical moments, including the American Revolution and the Women’s Suffrage Movement. Faneuil Hall has also been a stage for many political figures to speak, including Susan B. Anthony, John F. Kennedy, and Barack Obama.