Winter Date Ideas in Boston, Massachusetts

Boston offers a variety of winter-themed activities and romantic date ideas during the colder months.

Here are some winter date ideas for you to consider:

Ice Skating at Frog Pond:

Enjoy a classic winter activity by ice skating at the Boston Common’s Frog Pond. The Boston Common Frog Pond is a popular outdoor ice skating rink located in the heart of Boston Common, the city’s oldest public park.

The Frog Pond ice skating rink typically opens in mid-November and continues through mid-March, with the exact dates varying each year based on weather conditions. It’s a picturesque location, especially in the evening when the city lights add to the ambiance.

Winter Walk in Boston Common and Public Garden:

Bundle up and take a romantic stroll through the snow-covered Boston Common and Public Garden. The winter scenery can be magical, especially after a fresh snowfall.

During the holiday season, the Boston Common is adorned with festive decorations, creating a picturesque and joyful atmosphere for visitors.

Cozy Dinner at a Fireplace Restaurant:

Find a restaurant with a fireplace to add warmth and coziness to your dinner date. Many Boston establishments offer a charming atmosphere during the winter months.

Some restaurants in Boston that have a fireplace include the Fireplace restaurant in Brookline, Abe & Louie’s Steakhouse in Boston, Top of the Hub on the 52nd floor of the Prudential Tower as well as Grotto in Beacon Hill, just to name a few.

Igloo Dining:

A handful of restaurants and hotels in Boston offer igloo dining and igloo bars during the winter months. These Igloos are small, transparent, and often heated domes or igloo-like structures outdoors.

These structures are typically made of clear materials like plastic or glass, allowing guests to enjoy the surrounding views while being sheltered from the elements.

Igloo dining and igloo bars are particularly popular during winter months. The enclosed pods provide a way for guests to dine outdoors while staying warm and comfortable, creating a festive and cozy atmosphere.

Some restaurants offering igloo dining or bars in Boston include Lookout Rooftop on the roof of the Envoy Hotel, Woods Hill at Pier 4, 75 Liberty Wharf and Six West Broadway on top of the Cambria Hotel.

Sledding in Boston Parks:

Embrace the winter fun by going sledding in one of Boston’s parks. Bring your own sled and find a hill where locals gather for some fun in the snow.

Some popular sledding spots in Boston include Boston Common, the Arnold Arboretum in Jamaica Plain, Turkey Hill at Larz Anderson Park as well as Dorchester Heights.

Hot Chocolate Date:

Warm up with a hot chocolate date. Find a cozy cafe or chocolate shop that offers rich hot chocolate with various toppings and enjoy it together.

Or, you can visit a cozy bar with a fireplace and enjoy a nice hot toddy, which is boozy beverage made with a combination of whiskey, hot water, honey, and lemon.

Attend a Winter Festival:

Winter festivals in Massachusetts offer a variety of outdoor activities and community events that embrace the charm and beauty of the winter season.

Winter festivals are common in Massachusetts and typically include a mix of activities such as parades, fireworks, bonfires, live music and games.

Attend a Winter Concert or Show:

Check out winter performances, concerts, or holiday shows happening in Boston. Many theaters and concert venues host special events during the holiday season.

Some popular winter shows and concerts in Boston include the Nutcracker at the Boston Opera House and the Boston Pops Holiday Concert at Symphony Hall.

Night Skiing:

If you both enjoy skiing or snowboarding, plan a trip to one of the nearby ski resorts for some night skiing. Massachusetts has several options for winter sports enthusiasts.

Some ski resorts near Boston include Wachusett Mountain Ski Area in Princeton, Nashoba Valley Ski Area in Westford, Blue Hills Ski Area in Canton.

Wine Tasting:

Visit a local winery or wine bar for a cozy wine tasting. It’s a relaxing way to spend an evening together, savoring different wines and enjoying each other’s company.

Wine tastings provide a fun social setting where couples can talk and hang out in a relaxed environment. Discussing the different wines, their flavors, and your preferences can be a fun and interactive experience.

Museum Date:

Explore one of Boston’s museums or art galleries. It’s a great way to stay warm while immersing yourselves in culture and learning something new.

The exhibits and displays in museums can serve as excellent conversation starters. Discussing artworks, artifacts, or historical events can lead to interesting conversations and provide insights into each other’s interests and perspectives.

Museums often have a quiet and contemplative atmosphere, creating an intimate setting for a date. It allows you to enjoy each other’s company in a more relaxed and focused environment.

Remember to check for any specific seasonal events, festivals, or activities happening in Boston during your visit to make the most of the winter season.

If you are looking for ideas for a Valentine’s Day date, check out this article on things to do on Valentine’s Day in Boston.

“Things to Do in the Winter.” Boston Tea Party Ships & Museum,
McAleer, Kim. “22 best things to do in winter in Boston.” Time Out Magazine, 23 Oct. 2023,
“32 winter date ideas for couples.” Capital One, 8 Dec. 2022,

About William Briscoe

William Briscoe is a seasoned travel blogger and adventurer based in Massachusetts. With a passion for exploring hidden gems and sharing his travel experiences, Briscoe's website, "Mass Attractions," has become a go-to resource for those seeking seasonal attractions in Massachusetts. In addition to his website, William has contributed travel stories and articles to various travel publications, and his work has been featured in several magazines and online platforms. He also collaborates with tourism boards and travel companies to promote sustainable and responsible travel practices. William enjoys exploring the scenic beauty of New England, spending time with his family and two rescue dogs, and experimenting with classical New England recipes in his kitchen. He holds a degree in English Literature from Boston University, which he believes laid the foundation for his writing skills.

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