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Cape Cod Christmas Strolls,
Caroling & Tree Lightings
2025

Welcome to Holiday season on Cape Cod! It's time for Christmas strolls, village tree lighting ceremonies and caroling events in towns across the Cape!

And let's not forget ... shopping, visits with Santa, horse-and-carriage rides, and tasty treats offered up by local businesses and eateries.

Come join the festivities! 

Cape Cod Holiday Celebrations

Tree Lighting at Mashpee Commons

November 28, 2025
3:30 - 5:00 p.m.
On the plaza outside Siena at Mashpee Commons.

• Holiday caroling
  
  
• Appearance by Santa
  
  
• Mashpee Commons Tree Lighting
  
  
• Complimentary treats & hot chocolate
  
  
• More information here.

"Tis the Season in Orleans

November 28 -29, 2025
Various locations in Orleans

• Tree Lighting
  
  
• Santa arrives by boat
  
  
• Breakfast with Santa & Mrs. Claus
  
  
• Holiday Shopping Stroll
  
  
• Lots of other activities, too!
  
  
• More information here.

Lighting of the Lobster Pot Christmas Tree

November 29, 2025
5:30 p.m.
Lopes Square, Provincetown

• Made from 100+ lobster pots stacked over 2 stories high and decorated with ribbons, garland and thousands of festive lights, the Popko family's famous Lobster Pot Christmas Tree will put you in the Holiday mood for sure!

More info here.

Barnstable Village Winter Stroll

December 3, 2025  
6:00 - 8:00 p.m.
Along Main Street, Barnstable Village

• Holiday stroll on Main Street (Rt. 6A) in Barnstable village
  
  
• More information here.

Windmill & Tree Lighting in Brewster

December 5, 2025, 4 - 6 p.m.
4 p.m. to 6 p.m.
Drummer Boy Park in Brewster

• Illumination of the Christmas tree and windmill
  
  
• Caroling with the Brewster Eddy School Choir
  
  
• Santa arrives by Fire Truck

This event is part of the annual Brewster for the Holidays celebration.

More info here.

Community Carol Sing in Sandwich

December 5, 2025  
7:00 p.m.
First Church of Christ, Main Street in Sandwich

• Join the annual community Carol Sing on the steps of the church. Santa Claus will make a brief appearance.
  
  
• After the caroling, don’t forget to check out the Giants that are lighted up for all to see!

Wellfleet Tree Lighting & Sing Along

December 5, 2025, 4:00 - 5:00 p.m.
Town Hall in Wellfleet MA

• Tree lighting ceremony
  
  
•  Caroling with local musicians and special guest carolers from Wellfleet Elementary School
  
  
• More info here.

Caroling in Woods Hole Village

December 5, 2025
5:30 to 6:30 p.m.
Woods Hole Waterfront Park

• Christmas caroling 
  
  
• Sing along with the Solstice Singers
  

Harwichport Holiday Stroll & Tree Lighting

December 5 - 7, 2025
Various venues in Harwichport

• All weekend, stroll through Harwich Port businesses and organizations for dining, holiday cheer and shopping.
  
  
• Lots of family friendly events including tree lightings, caroling, fireworks, Santa's arrival and meet & greet, town band concert, and more.
  

Beginning this weekend through the end of December, the Christmas trees in all seven Harwich villages will be illuminated from dark to 10 p.m.

More info here.

Caroling & Cocoa at Chatham Bars

December 5, 12 & 19, 2025
5 - 6 p.m.
Chatham Bars Inn, Chatham

• Join carolers at the Chatham Bars Inn an hour of holiday cheer featuring traditional caroling and rich, decadent cocoa. 
  
  
• Open to guests, members and the local community (complimentary).
  

More info here.

Falmouth Holidays By The Sea

December 5 - 7, 2025
All weekend
Multiple locations in Falmouth

• Take the trolley from Woods Hole to the Holiday open house at Nobska Lighthouse
  
  
• Welcome seafaring Santa as he sails into Falmouth Harbor.
  
  
• Enjoy live music, dancing, shopping, and dining on Main Street.
  
  
• Share in the magic moment when the Village Green transforms into Santa's wonderland.
  
  
• And be sure not to miss the best and largest Christmas Parade in Southeast New England!
  

That's just some of the many special events taking place this weekend for "Falmouth Holidays by the Sea & Christmas Parade".

More info here.

Hyannis Main Street Holiday Events

December 6 & 7, 2024
All day
Main Street, Harbor Overlook and Hyannis Harbor

• "Sip & Shop" Holiday kickoff
  
  
• S’mores, singing, and Santa Claus arriving onboard an antique fire truck 
  
  
• Boat lighting at the harbor

More info here.

Hyannis Boat Parade

Christmas in Cotuit

December 6, 2025
10 a.m. to 5 p.m.
Multiple venues around the village of Cotuit

• Santa's arrival by boat at the town dock, followed by the tree lighting, caroling and cookies at Cotuit Village Green
  
  
• Other Christmas in Cotuit events - TBA

More info here.

Caroling at Eastham's Windmill Green

December 6, 2025 
4 p.m. to 5 p.m.
Windmill Green in Eastham

• Join the talented Nauset Honors Chorus in a sing-along of favorite Christmas songs.
  
  
• Free light refreshments
  
  
• More information here.

Sandwich Village Stroll

December 7, 2025
Noon to 5 p.m.
Sandwich Village

• A full afternoon of store open houses, performances, family activities and Santa's Village.  
  
  
• Lighting of the Glass Town Christmas Tree
  
  
• More info here.

Yarmouth Christmas Stroll & Tree Lighting

December 7, 2025
1 - 4 p.m.
Yarmouth Port Village Green

• Walk along Route 6A in Yarmouth Port, see the sights and grab a bite to eat.
  
  
• Enjoy trolley rides, live music and holiday treats.
  
  
• At 4 p.m. there'll be a tree lighting ceremony and caroling on the Village Green.
  
  
• More info here.

Old Yarmouth Inn at the Holidays

Centerville Christmas Stroll

December 7, 2025
Main Street in Centerville

• Shopping, goodies, and live music up and down Main Street.
  
  
• Santa and his elves return to their special workshop in the village.
  
  
• Will the ever-popular “flash mob” be making an appearance this year? Let's hope so!
  
  
• More info here.
  

West Barnstable Tree Lighting & Caroling

December 7, 2025
Begins at 5:00 p.m.
West Barnstable Village Green & 1717 Meeting House

• Tree lighting and caroling
  
  
• Santa arrives on the West Barnstable fire engine
  
  
• The Christmas Story and Carol Sing featuring a living nativity scene, the West Parish Hand Bell Choir, and music on the Mander Organ, followed by an informal gathering in Jenkins Hall with lots of good food and friendly people.
  
  
• More information here.

Chatham Christmas Stroll

December 12 - 14, 2025
Main Street in Chatham

• Light parade with Santa
  
  
• Lighting of the town Christmas tree
  
  
• Musicians, street performers and shopping on Main Street
  
  
• Santa's Workshop at the Chatham Chamber.
  
  
• And returning this year, the horse and carriage ride (located outside Town Hall).
  
  
• More info here.

These events are part of Chatham's annual "Christmas By The Sea" celebration.

Dennis Village Stroll

December 14, 2025
Noon to 5:00 p.m.
Dennis Village Green and Rt. 6A in Dennis

• Visits with Santa, giveaways, children's activities, live music and lots more

More info here.

Annual Carol Sing

December 23, 2025
3:00 p.m.
Performing Arts Center, 95 Southern Eagle Cartway, Brewster MA

• Delightful mix of traditional and modern carols with ensembles of Arts Empowering Life.
  
  
• Join in singing your favorites.
  
  
• Refreshments provided.
  
  
• Free admission.
  
  
• More info here

Happy Holidays to One and All!

 
>>See: Lots more fun things to do on Cape Cod in December

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