Answers You Need
Have a question? Whether you're planning your next visit, curious about our amenities, or need assistance with a booking.
Visit FAQs page
There’s something special about Christmas on Cape Cod, and few places capture the season quite like Chatham. Twinkling lights line Main Street, storefronts dress up for the holidays, horse-drawn carriages make their way through town, and the heart of Chatham transforms into a classic New England Christmas scene.
This year, Chatham Christmas by the Sea returns December 11–13, 2026, bringing a full weekend of holiday traditions, local shopping, family-friendly activities, and festive celebrations to downtown Chatham.
And when you stay at Chatham Wayside Inn, you don't just visit the Christmas Stroll—you stay right in the middle of it.
What Is Chatham Christmas by the Sea?
Christmas by the Sea, often referred to as the Chatham Christmas Stroll, is one of Chatham's signature holiday traditions. Held each December, the weekend brings residents and visitors together to celebrate the season throughout Main Street and downtown Chatham.
The 2026 celebration is scheduled for Friday, December 11 through Sunday, December 13, with holiday shopping, festive activities, and classic small-town traditions planned throughout the weekend.
If you've ever imagined spending the holidays in a picturesque New England seaside town, this is about as close as it gets.
Christmas by the Sea Traditions to Look Forward To
While the complete 2026 schedule will continue to take shape as the event approaches, Christmas by the Sea is known for turning downtown Chatham into a weekend-long holiday celebration.
Past celebrations have kicked off Friday evening with a children's light parade along Main Street, followed by the Christmas tree lighting at Sears Park. Other traditions have included horse-drawn carriage rides, visits with Santa, live entertainment along Main Street, holiday shopping, and special events at local businesses.
The result is a holiday weekend that feels distinctly Chatham: festive without losing the relaxed coastal character that makes the town special year-round.
Holiday Shopping on Main Street
Christmas by the Sea is also one of the best weekends of the year to explore downtown Chatham shopping.
Main Street's locally owned boutiques, galleries, gift shops, and specialty stores make it easy to find something more memorable than the typical holiday shopping haul. During the Christmas by the Sea weekend, many businesses embrace the celebration with decorated storefronts, seasonal specials, and extended festivities.
Best of all, when you stay at Chatham Wayside Inn, Main Street is quite literally outside your door. The Inn's central location at 512 Main Street means guests can step outside and begin exploring downtown without having to build their weekend around driving and parking.
Experience Cape Cod in the Off-Season
The Chatham Christmas Stroll may be the centerpiece of the weekend, but December is also an opportunity to experience a completely different side of Cape Cod.
Gone are the busy summer crowds. In their place are peaceful beaches, quiet coastal roads, cozy restaurants, and a more relaxed downtown atmosphere. Winter visitors can take a brisk walk near Chatham Lighthouse, explore the shoreline, browse Main Street at their own pace, or simply enjoy a slower weekend by the sea.
It's one of the reasons a winter getaway to Chatham, MA can feel so different from a traditional Cape Cod vacation. You're still surrounded by the places that make Chatham special—just at a quieter, cozier time of year.
Make a Weekend of It at Chatham Wayside Inn
If you're searching for a hotel for the Chatham Christmas Stroll, location matters.
Chatham Wayside Inn sits directly on Main Street in the heart of downtown Chatham, putting guests steps from the shops, restaurants, galleries, and holiday activities that make Christmas by the Sea worth experiencing.
Instead of driving into town for the festivities and worrying about parking, you can settle into your room and explore much of the weekend on foot. Catch the holiday activity along Main Street, browse the shops, stop back at the Inn when you need a break, and head out again when you're ready.
And when hunger strikes, you don't have to venture far.
Warm Up at Wild Goose Tavern
Located onsite at Chatham Wayside Inn, Wild Goose Tavern makes an easy addition to a Christmas by the Sea weekend.
The downtown Chatham restaurant serves lunch and dinner with fresh coastal flavors, American tavern favorites, and handcrafted cocktails—all without requiring hotel guests to get back in the car.
That means your holiday itinerary can be refreshingly simple: stroll Main Street, shop for gifts, enjoy the festivities, then head back to Wayside and settle in for dinner or drinks at the Goose.
Turn the Chatham Christmas Stroll Into a Holiday Getaway
Christmas by the Sea only comes around once a year, and staying overnight gives you the chance to enjoy Chatham beyond a few hours of festivities.
Arrive Friday and experience the start of the celebration. Spend Saturday exploring Main Street, shopping, dining, and taking in the holiday atmosphere. Then enjoy a slower Sunday morning before one last walk through town.
With Chatham Wayside Inn's Main Street location, your accommodations become part of the experience rather than simply a place to sleep.
If a festive Cape Cod escape is on your holiday wish list, consider making a weekend of Christmas by the Sea, December 11–13, 2026. Staying at Wayside puts the heart of Chatham—and much of the holiday magic—right outside your door.
Explore accommodations at Chatham Wayside Inn and start planning your Christmas by the Sea getaway.
Frequently Asked Questions About Chatham Christmas by the Sea
When is the Chatham Christmas Stroll in 2026?
Chatham Christmas by the Sea is scheduled for Friday, December 11 through Sunday, December 13, 2026, in downtown Chatham, Massachusetts.
Where does Chatham Christmas by the Sea take place?
The celebration is centered around Main Street and downtown Chatham, with activities taking place throughout the village.
What happens during the Chatham Christmas Stroll?
Christmas by the Sea traditionally features holiday shopping, family activities, decorated storefronts, and seasonal entertainment. Previous editions have included a children's light parade, the Sears Park tree lighting, horse-drawn carriage rides, visits with Santa, and live entertainment along Main Street. Specific 2026 activities and times are subject to the official event schedule.
Is Chatham Christmas by the Sea family-friendly?
Yes. Christmas by the Sea is designed as a community-wide holiday celebration with traditions and activities suitable for families, including children's activities and Santa appearances.
Where should I stay for the Chatham Christmas Stroll?
Travelers who want to be close to the festivities can stay at Chatham Wayside Inn at 512 Main Street. Its downtown location puts guests steps from shops, restaurants, galleries, and many of the Christmas by the Sea activities.
Is there a restaurant at Chatham Wayside Inn?
Yes. Wild Goose Tavern is located onsite at Chatham Wayside Inn and serves lunch and dinner along with handcrafted cocktails and coastal-inspired and American tavern fare.
Is December a good time to visit Chatham, MA?
December offers a quieter way to experience Chatham and Cape Cod, with fewer crowds, easier access to downtown, peaceful coastal scenery, and seasonal events such as Christmas by the Sea.
Should I book my Chatham Christmas Stroll hotel in advance?
Planning ahead is a good idea when traveling for a specific event weekend. Christmas by the Sea takes place during one designated December weekend, so booking accommodations early provides more choice when planning your stay in downtown Chatham.
