There’s something special about Fall on Cape Ann. When the summer crows fade, and the crisp ocean air settles over Gloucester Harbor, and days spent exploring the coast give way to cozy evenings fireside.
From colorful fall hikes and seasonal dining to Halloween celebrations, live music, holiday traditions, and peaceful mornings overlooking the water, fall and winter offer an entirely different way to experience Gloucester. If you’re planning a weekend getaway or looking for another reason to return to the coast, here are a few of our favorite ways to embrace the seasons at Beauport Hotel Gloucester and around Cape Ann.
Settle In for Beauport Sessions
This season, the soundtrack to your stay is getting a little cozier.
We’re introducing Beauport Sessions, bringing weekly live music, Tuesday evenings from 6:00PM–9:00PM, to the heart of the hotel. Settle into a fireside seat, order your favorite cocktail, and turn up your weeknight vibes to live sounds as evening falls over Gloucester Harbor.
It’s the perfect reason to stay awhile, consider this your invitation to add some fun to those cooler days, sip something special, and enjoy a new rhythm at Beauport.
Turn up the vibes, fireside.
Taste the Season at 1606
Sweater weather calls for something warm at the table. At 1606 Restaurant & Oyster Bar, seasonal flavors meet coastal inspiration, with thoughtfully crafted dishes that celebrate the changing seasons.
Settle in for a cozy evening overlooking the water, sip on a seasonal cocktail, and savor the flavors of New England, all with nowhere else you need to be.
Halloween Takes Over the Harbor
From sea to shore, October 31st brings two distinct ways to celebrate Halloween with Beauport.
During the day, little ghosts, goblins, witches, and wizards can climb aboard Beauport Cruiselines’ Boo-Port Spooktacular from 11:00AM–12:30PM. The family-friendly Halloween cruise features pumpkin decorating, crafts, treats, live DJ entertainment, costumes, and plenty of festive fun while cruising Gloucester Harbor. (Link Cruise)
Then, after dark, it’s time for the grown-ups.
Dress to impress for the Beauport Hotel Halloween Soirée, happening from 8:00PM–11:00PM. The 21+ celebration brings live DJ entertainment, bewitching craft cocktails, late-night bites from 1606 Restaurant & Oyster Bar, and a Best Costume Contest to the oceanfront. A portion of proceeds benefits Mass General Brigham Cancer Institute.
Explore Cape Ann in Full Color
Some of Cape Ann’s best views arrive after summer.
For a quintessential fall walk, Ravenswood Park offers 600 acres and 10 miles of carriage paths and trails through woodland, wetlands, fern-covered boulders, and scenic overlooks. The two-mile Ledge Hill Trail is an approachable option, while other routes lead toward views of Gloucester Harbor. The Trustees of Reservations
For something a little more coastal, head to Rockport and Halibut Point State Park, where trails wind past a historic granite quarry toward dramatic rocky coastline and wide-open Atlantic views. The neighboring Halibut Point Reservation has approximately 2.5 miles of trails and is open daily from sunrise to sunset. The Trustees of Reservations
Closer to Gloucester, Rafes Chasm Park is another scenic option for a shorter coastal outing, with a woodland approach opening onto Cape Ann’s rugged granite shoreline.
Pack an extra layer, lace up your walking shoes, and make a morning of it before returning to Beauport for something warm.
Discover Cape Ann’s Creative Side
Fall also puts Cape Ann’s longstanding arts community on full display.
Cape Ann Plein Air welcomes 36 juried artists to paint the landscapes of Gloucester and surrounding Cape Ann communities, with demonstrations, special events, a Quickdraw competition, and a Gala & Art Sale throughout the week.
For a little history with your art, Cape Ann Museum offers another way to spend a crisp afternoon exploring the stories, art, and culture that have shaped this corner of the coast.
Stay for Gloucester’s Holiday Magic
As autumn gives way to winter, Gloucester trades fall foliage for twinkling lights and hometown holiday traditions.
November and December bring Gloucester’s Holiday Celebrations, with seasonal shopping, tree lightings, parades, and festivities throughout the city. One tradition worth planning around is the Middle Street Walk, held on the second Saturday in December. Historic buildings and cultural organizations along Middle Street and Harbor Loop open their doors for holiday fairs, workshops, music, tours, and family activities before the day culminates in the Lobster Trap Tree Lighting at Harbor Loop.
It’s a distinctly Gloucester way to celebrate the season and an easy addition to a winter weekend at Beauport.
Cozy Up on the Coast
Of course, not every fall or winter getaway needs an itinerary.
Sometimes the best Cape Ann days begin with a slow breakfast, continue with a walk along the harbor, and end curled up beside the fireplace as the ocean stretches beyond the windows.
This holiday season, make your getaway a little more special with our Home for the Holidays package at Beauport Hotel Gloucester. Enjoy a restful night by the water, breakfast for two at 1606 Restaurant & Oyster Bar, and two festive Hot Chocolate Kits, complete with mugs, cocoa bombs, and marshmallows. Available November 23rd through January 4th, it's a sweet way to settle into the season.
Make Beauport Hotel your home by the water and experience Gloucester at a quieter pace, with ocean views, seasonal dining, fireside cocktails, live music, and some of Cape Ann’s most beautiful places just beyond our doors.
Cozy days, crisp coastal air, and a season worth slowing down for.