11 Best Things to Do in Fenway to Make the Most of Your Trip

Nestled within the heart of historic Back Bay Boston, “The Fens” is a neighborhood originally named for its wetland ecosystem. While remnants of the marshland are still visible in its parks, the Fenway neighborhood beckons with its unique blend of cultural charm, lively energy, and a dash of classic New England allure. Renowned for being home to the iconic Fenway Park, where the crack of baseball bats mingles harmoniously with the vibrant city buzz, this neighborhood is a captivating tapestry of experiences waiting to be unraveled.

Quick Answer Guide: 11 Best Things to Do in Fenway

‌Top Things to Do in Fenway‌

‌Best Things to Do During the Day in Fenway‌

‌Best Things to Do Outdoors in Fenway‌

  • Best for working off any Fenway Franks you had at Fenway Park - Biking
  • Best for birders with a keen eye - Bird Watching

‌Best Things to Do at Night in Fenway‌

‌Free Things to Do in Fenway‌

Top Things to Do in Fenway

A blend of history, culture, and urban vibrancy, the Fenway neighborhood of Boston has become synonymous with Boston’s rich baseball heritage as home to the iconic Fenway Park. Whether you’re catching a game, delving into art and culture, exploring lush green spaces, or indulging in its nightlife, the Fenway district is quintessentially Boston, and easily accessible via the “D” branch of the Green Line, the subway system of the Massachusetts Bay Transportation Authority.

1. Fenway Park

  • Perfect For:‌ Baseball fans
  • Website:https://www.mlb.com/redsox/ballpark
  • If You Go:‌ Enjoy pre- and post-game bevvies at the Cask ‘n Flagon on Brookline Avenue, a must-visit for Sox fans since 1969.

No trip to Boston is complete without the No. 1 place to visit in Fenway: Fenway Park — the place I take everyone who visits from out of town, even if they are Yankees fans. One of the best things to do in Fenway is touring the park or seeing a Boston Red Sox game at Fenway Park will immerse you in the hallowed grounds and evoke the spirit of America’s favorite pastime. Walk through the famous Player’s Entrance, where legends like Babe Ruth have stepped onto the diamond for over a century, and see the fabled Pesky’s Pole right field foul pole, just 302 feet from home plate and one of the shortest distances to a foul pole in Major League Baseball. With its meticulously maintained Green Monster left-field wall and intimate seating — including the “red seat,” where the longest home run ever hit at Fenway landed in the right-field bleachers — Fenway Park offers an unparalleled baseball experience that brings you remarkably close to the action. Even if you don’t catch a baseball game, sign up for any of the Fenway Park Tours offered outside of game days to get a closer look at the ballpark’s history, dating back to 1912.

2. Museum of Fine Arts

All Getaways
Paul Marotta/Getty Images Entertainment/GettyImages
  • Perfect For:‌ Connoisseurs of fine arts
  • Website:https://www.mfa.org
  • If You Go:‌ The museum is closed on Tuesdays.

Widely considered one of the best art museums in the United States, the MFA stands as a testament to human creativity and expression through the ages with a collection of over 450,000 works of art, including masterpieces from ancient civilizations to contemporary creations. Located just off Boylston Street on Huntington Avenue, step into galleries adorned with treasure from renowned artists like Van Gogh, Monet, and Rembrandt and explore captivating exhibitions that illuminate the diversity of cultures, from the intricacies of Asian art to the evocative power of African sculptures. Guided tours unveil stories behind the art, and visitors can also participate in workshops that allow them to channel their inner artists.

3. Isabella Stewart Gardner Museum

All Getaways
Spencer Grant/Archive Photos/GettyImages
  • Perfect For:‌ Art aficionados
  • Website:https://www.gardnermuseum.org
  • If You Go:‌ Thirteen works of art were stolen from the museum in 1990, and empty frames remain hanging in the museum, awaiting their return.

The Gardner Museum is a cultural treasure with a rich history that reflects the passion and vision of its founder, Isabella Stewart Gardner. Known for its unique architecture and stunning collection of artwork, the museum is also the site of one of the world’s largest art heists that left empty frames in its wake — literally! Although still unsolved, with pieces from Vermeer and Degas remaining lost to the masses, the museum continues to thrive as a cultural hub, hosting exhibitions, performances, and educational programs. Modeled after a 15th-century Venetian palace, the museum is a must do in Fenway. It is filled with the eclectic tastes of Gardner, from European, Asian, and American art, featured in galleries adorned with paintings, sculptures, decorative arts, rare books, and textiles.

Best Things to Do During the Day in Fenway

Originally a tidal marshland with waterways that flowed into the Charles River, The Fens was transformed into a designed park system by landscape architect Frederick Law Olmsted, famous for his work on New York City’s Central Park. Creating a series of interconnected parks that includes the Boston Common and Boston Public Garden, Olmsted turned the tidal marsh into a picturesque green space, just ripe for fun in the sun, and the best things to do during the day in Fenway (besides catching a game at Fenway Park) involve its parks.

4. James P. Kelleher Rose Garden

All Getaways

Uncover a symphony of colors, fragrances, and natural elegance at the Kelleher Rose Garden, an enchanting botanical jewel. This hidden gem of Boston surrounds you with a breathtaking array of rose varieties, each carefully cultivated to showcase nature’s artistic prowess. Of all the activities in Fenway, this may be the most peaceful as you lose yourself in contemplation in the garden’s serene escape from the bustle of the city. If you are only making a day trip to Boston and want to enjoy a nice afternoon, this is a great choice for an activity.

5. Back Bay Fens

All Getaways

The calm network of meandering waterways, tree-lined pathways, and lush green expanses of the Back Bay Fens await your exploration. Wander alongside shimmering ponds, where graceful swans glide and vibrant flowers kiss the water’s edge. The Fens offer more than just natural beauty. Its thoughtfully designed park system plays host to an array of recreational activities, from picnics to leisurely bike rides, and you can engage with history as you stroll past historic monuments and sculptures that pay homage to Boston’s rich heritage.

Best Things to Do Outdoors in Fenway

Yes, the best things to do during the day in Fenway are also the best things to do outdoors … Fenway’s name is a pure indication that this neighborhood is all about its green spaces. Boston’s Emerald Necklace is perfect for outdoor activities, and Bostonians take advantage of the park system every day of the week (especially during warm-weather months, as Boston winters are notoriously harsh and keep us locked indoors). Do I wax poetic about the Emerald Necklace? Yes! Because it really is one of Boston’s finest attributes.

6. Biking

All Getaways

Boston has a network of more than 170 miles of on-street bike lanes, bike paths, and shared bike routes — and thank goodness because before these paths were added, cycling through Boston’s notorious traffic was a real risk. One of the city’s newest bike paths is the Fenway Multiuse Path. Connecting the Emerald Necklace main pathways to Lansdowne Station, Fenway Park, and Beacon Street leading to Kenmore Square, the path extends 1,700 feet and allows visitors to explore Fenway on two wheels.

7. Bird Watching

All Getaways
kiun ink / 500px/500px/GettyImages

Not all of Boston’s sightseeing is dedicated to its history (and admittedly, Fenway’s history beyond the ballpark is not as exciting as its other neighborhoods). The Fens is actually home to a variety of bird species, making it a popular destination for birdwatchers. From graceful swans to great blue herons, vibrant red cardinals to red-winged blackbirds, and dabbling mallards to iridescent-winged European starlings, Boston provides habitat for various bird species throughout the year.

Best Things to Do at Night in Fenway

As the sun sets, Fenway transforms into a captivating playground of nighttime enchantment. Fenway’s nighttime canvas is painted with a blend of sports, culture, entertainment, and culinary delights. While the nightlife doesn’t go into the wee hours like other big cities across the U.S., thanks to Boston’s Blue Laws, you can still indulge in the diverse culinary scene, whether it’s savoring a gourmet dinner or grabbing late-night-ish bites from local eateries that have been staples in the city for decades. When the night comes to a close, stay at a host of hotels near Fenway Park, including the Hotel Commonwealth, nearest to the action. (I especially love Hotel Commonwealth’s ballpark-facing rooms.)

8. Symphony Hall

All Getaways
Santi Visalli/Archive Photos/GettyImages
  • Perfect For:‌ Music lovers
  • Website:https://www.bso.org
  • If You Go:‌ Take a free behind-the-scenes tour, offered on select dates.

Immerse yourself in the heart-stirring melodies performed by the Boston Symphony Orchestra in a hall world-renowned for its acoustics. The hall’s neoclassical beauty includes intricate detailing and a majestic organ, providing an immersive setting that ensures every performance is a captivating journey of emotion and sound. The Boston Pops, as Bostonians lovingly call the orchestra, was founded in 1881 and is one of the premier orchestras of the U.S., graced by the batons of esteemed conductors like Charles Munch, James Levine, and John Williams, the latter of whom composed the musical themes of “Star Wars,” “Indiana Jones,” and even the bah-bum of “Jaws.”

9. Lansdowne Street

All Getaways
Maddie Meyer/Getty Images Sport/GettyImages

Whether staying in Fenway or any neighborhood in Boston, one of the best places to visit in Fenway is Lansdowne Street, a pulsating artery of Boston’s nightlife scene. As twilight descends, Lansdowne Street comes alive with a kaleidoscope of neon lights and the rhythmic beats of live music venues and is consistently the place to be for dancing, drinking, and mingling with locals. From legendary nightclubs like the House of Blues to intimate music halls, this vibrant strip offers unparalleled options for an electrifying night out. It’s also filled with a wide variety of restaurants and bars, including the Bleacher Bar, situated beneath the bleachers at Fenway Park and offering a view of the outfield through a large window.

Free Things to Do in Fenway

Discover the Fenway neighborhood through a range of free activities that embrace the essence of the vibrant district, from meandering through the Fenway Victory Gardens, wandering along the Back Bay Fens’ tranquil pathways, and engaging with the neighborhood’s artistic soul as you encounter sculptures, monuments, and architectural gems that tell stories of Boston’s past. Amidst charming storefronts and green havens, you’ll find an array of experiences that showcase Fenway’s character without breaking the budget.

10. Berklee College of Music’s Summer in the City Concerts

All Getaways
Paul Marotta/Getty Images Entertainment/GettyImages

Established in 1945, Berklee College of Music has become one of the world's most prestigious and influential music institutions. Berklee lends an airy of artistry to Fenway, with students zig-zagging through the streets carrying an array of musical instruments and frequently busking on street corners any day to keep music in the air any day of the year. But every May through early October, Berklee College of Music students, faculty, and alumni gather to perform hundreds of free contemporary and classic music concerts and answers the questions of what to do in Fenway.

11. Emerald Necklace

All Getaways
  • Perfect For:‌ Enjoying the great outdoors
  • Website:https://www.emeraldnecklace.org
  • If You Go:‌ As the saying goes, “If you don’t like the weather in New England, just wait a few minutes.” Check the forecast to be sure you’re wearing the right attire.

I said it once, and I’ll say it again: Olmsted’s creation of Boston’s Emerald Necklace means visitors can explore a chain of lush parks and green spaces that weaves its way through the entire city like a necklace. The urban oasis hosts a calendar of cultural events, from outdoor concerts to community gatherings, many of which are free throughout the year. I’ve seen up-and-coming artists perform and free concerts by big names in music — it’s one of the best things to do in Fenway!

From the crack of baseball bats at Fenway Park to the serene lushness of its parks, Boston's Fenway neighborhood truly offers a blend of experiences that'll leave you wanting more. Whether you're an art enthusiast, a history buff, a nature lover, or just someone looking to soak in the vibrant city vibes, Fenway has your back. Hop on the "D" branch of the Green Line and let this neighborhood's unique blend of cultural charm and lively energy sweep you off your feet.