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What to do in Fenway this Winter

Visit The Fenway this Winter for Ice Skating, Dining, Shopping, and More

Looking for something fun to do this winter to distract yourself from the cold? Why not explore The Fenway in Boston! This historic neighborhood is home to one of the most famous ballparks in the world, but there’s much more to do here than just watch the Red Sox play. There’s plenty of shopping, nightlife, and entertainment to keep the winter chill away.

Whether you’re traveling with friends or the whole family, you’ll find lots to do in The Fenway. Check out our guide to the neighborhood so you can navigate like a local!

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Skate the Afternoon Away

Fenway’s newest addition, The Rink at 401 Park, is an awesome reason to dig out your old skates and bundle up a little extra. It’s a massive ice rink right in the heart of the neighborhood that transforms into a beautiful green space during the warmer months. Go for an hour or two (or until your hands are too cold to keep skating) and head next door to either Trillium Fenway or Time Out Market.

We love the extensive craft beer selection at Trillium, which is a well-established Boston-based brewery. If beer isn’t your thing, Time Out Market is sure to have something that’ll please even the pickiest of eaters. It’s a 25,200-square-foot galleria with 15 different restaurants and vendors to choose from. We’re particularly fond of Monti, where the James Beard Award winning chef serves up some mouth-watering Roman-style pizza. Want seafood instead? Don’t miss Saltie Girl and their gourmet lobster rolls.

Shop ‘Til You Drop

Over the past few years, The Fenway has grown into a shopping destination in the city. If it’s simply too cold to skate outside, why not peruse the many stores in the neighborhood? CB2, one of the newest openings, is a great spot to start if you’re interested in home improvement. From furniture to home accessories, there’s a great selection of items you can spruce up your house with available here.

For the outdoorsy types, REI offers an awesome selection of gear, warm coats, and other essentials for exploring the great outdoors. Be sure to pick up some rare wine at The Wine Press or craft beer at Fenway Beer Shop while you’re at it!

Browse Art Galleries

Sometimes, the best way to spend a day is cozy and warm inside a museum. The Museum of Fine Arts is The Fenway’s premier art museum and an easy place to spend several hours. There is an impressive selection of rotating exhibitions, galleries, and events at all times. We also love the Isabella Stewart Gardner Museum, a neighborhood gem tucked away a mere block from the MFA. This is a much smaller museum and it’s perfect for you and a loved one to explore together on a blustery winter day.

Check Out the Neighborhood Nightlife

The Fenway never sleeps, even in the dead of winter. Besides iconic sports bars that have been a staple of the neighborhood for decades, there are lots of newer venues that attract both college students and young professionals. We recommend sipping a glass of wine at Nathálie if you’re looking for a relaxed atmosphere. Fool’s Errand right around the corner is a quirky bar that serves up unique cocktails that you’re not likely to find anywhere else. Go there for a snack and a drink—you don’t want to miss it.

If you’re ready to dance the night away, head over to the House of Blues to see a live show! They have an impressive calendar filled with well-known artists and bands, so be sure to get your tickets ahead of time.

Whether you visit for a day or stay for a weekend, you’re bound to have a great time in The Fenway. It’s easy to get to from our South Station bus terminal: simply hop on the Red Line to Park Street and switch trains to the Green Line outbound to Riverside. In just minutes, you’ll be in The Fenway!

Ready to plan your adventure in the city? We sure are!

Download C&J's guide to top Boston attractions