While the days are shorter and colder weather is setting in, there’s still so much to see and do on your waterfront!

Explore miles of Boston’s Harborwalk, warm up at a local business, or tap in to virtual events at home. Take our recommendations for dining, art & light installations, and activities to help you make the most of the waterfront all winter long. Whatever you choose, go ahead and #BundleUpBoston, and enjoy your waterfront!

Events & Activities



Winter Wander on Peddocks Island

Experience an unforgettable winter day as you wander the trails of Peddocks Island in search of winter tracks and traces. Enjoy a guided walk, play in the snow (if the weather cooperates), or join us by the fire for s’mores by our fire pit.

  • Saturday, February 24, 2024 | 11:00pm -3:30 pm | REGISTER


Revelry and Revolution: An Evacuation Day Harbor Cruise

Learn the real history of the British evacuation of Boston in 1776 on a harbor excursion featuring live historical narration, live music, and close-up views of Boston Light: America’s first light station.

  • Saturday, March 23, 2024 | 11:00pm -3:30 pm | REGISTER


Revolutionary Harbor Lecture Series

Join the National Parks of Boston for this special winter lecture series running monthly, January through March.

  • What’s the Tea? The Boston Tea Party’s Impact on Boston and its Harbor | Tuesday, February 13, 2024 | REGISTER

  • Women’s History on the Boston Harbor Islands: The Great Brewster Journal | Wednesday, March 20, 2024 | REGISTER


Merry Moakley at Moakley Park

Join us for a family-friendly evening of festive fun with pizza, music, hot cocoa, crafts, free books, photos, games, and more.

  • Thursday, December 7, 2023 | 3:30 – 6:00 pm


11th Annual Waterfront Ice Sculpture Stroll

Our signature Waterfront Ice Sculpture Stroll is back! Get ready to count down to 2024 with more than 30 ice sculptures hosted by businesses and cultural sites across the waterfront – the largest Stroll EVER!


Friends of the Boston Harbor Islands New Year’s Day Boat Trip to Thompson Island

Join the Friends of the Boston Harbor Islands for a New Year’s Day boat trip to Thompson Island!

Enjoy a 45-minute boat ride through the Boston Harbor Islands and a panoramic view of the Boston skyline. Explore Thompson Island’s meadows, forests, beaches, and 40-acre salt marsh and learn about its intriguing history.

  • Monday, January 1, 2024 | 12:00pm -4:00 pm


Winter Wildlife Cruise

Grab your camera and binoculars and join park rangers and local naturalists to observe animals who make their wintertime home in Boston Harbor and around the outer Harbor Islands.

  • Saturday, January 20, 2024 | 11:00pm -3:30 pm


New England Boat Show

The 2024 Discover Boating New England Boat Show has a wide selection of boats, an abundance of must-see attractions, and fun features for all ages.

  • Wednesday-Sunday, January 10 – 14, 2024 | 10:00am – 2:00 pm | LEARN MORE


Winter Warmer at Moakley Park

Come to Moakley Park for a free, fun afternoon complete with warm drinks, yummy snacks, games, crafts, and more: Enjoy s’mores, popcorn, and hot cocoa Catch a musical performance Make Valentines for community elders Play yard games like Spike Ball & Cornhole Pick a book to take home Share your favorite Moakley memories & chat with friends around a fire.

  • Saturday, February 10, 2024 | 2:00 pm-4:00 pm | REGISTER



Explore Your Waterfront


Hold on to your handwarmers — the Seaport’s been shaken up in a giant snow globe and transformed into a magical winter getaway. Find gifts, treats, activities, and plenty of surprises in this one-stop wonderland you can enjoy all season.


Boston’s Black Heritage Trail

The Black Heritage Trail® is a 1.6 mile walk through the heart of Boston’s Beacon Hill neighborhood. The trail showcases residences and community buildings associated with a Black community that thrived on, and near, the north slope of Beacon Hill before, during, and after the American Civil War.


Art & Lights

Christopher Columbus Waterfront Park Holiday Trellis Lights

Bundle up and enjoy the the ambiance of the Christopher Columbus Parks iconic trellis ablaze in blue lights to commemorate the Holiday Season!


Ship Lights at Martin’s Park

Martin’s Park at the Smith Family Waterfront is a climate-resilient park built in memory of eight-year-old Martin W. Richard, the youngest victim of the 2013 Boston Marathon bombing. The accessible park provides play opportunities for children, families, and visitors of all abilities. The wooden play ship is the centerpiece of the space that will be lit for the holidays.


Hatchling on The Greenway

Created by interdisciplinary design team Studio HHH, Hatchlings is a 100% solar-powered installation that pays joyful homage to one of Boston’s architectural gems and envisions a brighter, more environmentally sustainable future for our city. This creative activation will provide Bostonians with an experiential destination during the coldest months of the year while showcasing an innovative and sustainable approach to holiday lights.


ICA Free Thursday Nights

The ICA is free for all visitors every Thursday evening. Tickets for Free Thursday Nights will be available at 10 AM on that Thursday morning.

Fitness and Wellness

Winter Harbor Hikes or Runs

Start your year off on the right foot with a self-guided walk along Boston’s Waterfront. Check out one of four recommended routes around the harbor to get outside and get moving!



Support our programs!

Boston Harbor Now is a 501(c)(3) nonprofit organization. Our programs would not be possible without the support of our generous donors. We hope you will consider joining your neighbors with a gift in support of our community programming.