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Cape Cod Holiday Events & Strolls

Updated for 2019

It’s the most magical time of the year, and we have your guide to staying in the holiday season all month long! Here is our list of Cape Cod Holiday Events & Strolls updated for 2019!


Santa Photos at the Cape Cod Mall

Location: The Cape Cod Mall, Hyannis

Dates: November 15th – December 24th

Website: Cape Cod Mall Santa Photos

Details: The Cape Cod Mall is the place to get your picture taken with Santa and let him know what you would like for Christmas. This year Santa is located at the Macy’s Men’s Court. Santa will be at his post Monday to Saturday 10:00 am – 9:00 pm and Sunday from 11:00 am to 6:00 pm (with a few exceptions, check website).

2019 Spectacle of Trees

Location: Cape Cod Mall (outside of Ten Pin Eatery), 769 Iyannough Road

Date(s): November 24th – December 14th

Website: Spectacle of Trees

Details: Purchase your tree bucks either at the display or online, then put the tree bucks in the box for the tree decorated by the non profit you would like to support and enter to win all of the goodies on the tree! This is a fun and festive way to support the non profit of your choosing and potentially win some pretty amazing prizes!

Annual Cape Cod Enchanted Village

Location: The Cape Codder Resort, Hyannis

Date(s): Saturday, November 30th – December 23rd

Website: Annual Cape Cod Enchanted Village

Details: Catch the Cape Codder Resort’s Enchanted Village holiday display from November 30th to December 23rd to get you into the holiday spirit this year! From December 6th to December 22nd you can catch Santa and carolers on Friday, Saturday and Sunday at the Enchanted Village. There are also free concerts open to the public, check their website for details.

Hyannis Village Christmas Stroll

Location: Main Street, Hyannis

Date(s): Saturday, December 7th  11:00 am – 6:00 pm

Website: Hyannis Village Christmas Stroll

Details: Start your day by having breakfast with Santa at the British Beer Company (ticketed event with two seatings available) and enjoy the holiday cheer all day long throughout Main Street. Santa arrives by antique fire truck to greet all of the good boys and girls at noon on the corner of Main Street and Winter Street. There are plenty of fun and free activities including a petting zoo!

Harbor Lighting / Boat Parade

Location: Hyannis Harbor

Date(s): Saturday, December 7th 4:00 pm – 5:30 pm

Website: Harbor Lighting / Boat Parade

Details: Boats all lit up for the holidays parade down the harbor for all to enjoy before Santa makes his arrival in a police boat! Santa will dock at about 5:00 pm and arrive at his shanty where he will greet all believers (and non believers).


Brewster for the Holidays

Location: Throughout the town of Brewster (mainly along route 6A)

Date(s): December 6th – December 8th

Website: Brewster for the Holidays 2019

Details: Brewster for the Holidays is kicked off on Friday at 4 pm at Drummer Boy Park with the annual lighting of the tree and windmill! Santa will be there along with refreshments and plenty of holiday cheer. Check out the website for all the details so you do not miss any of the holiday fun!


Chatham’s Christmas by the Sea Stroll Weekend

Location: All along Main Street, Chatham

Date(s): December 13th – December 15th

Website: Chatham’s Christmas by the Sea Stroll Weekend

Details: The Christmas fun begins on Friday, December 13th with a light parade and caroling at 5:45 pm that starts outside of Carmine’s Pizza on Main Street and ends at Kate Gould Park with the annual tree lighting. Check out the Chatham Christmas by the Sea Stroll website for a calendar of events going on throughout the weekend.


Santa Visits Patriot’s Square

Location: Patriot’s Square (Route 134)

Date(s): December 7th 1:00 pm

Website: Santa Visits Patriots Square

Details: Santa touches down in Patriot’s Square on December 7th by helicopter to visit with all the good boys and girls that wish to come and say hello!

Dennis Christmas Stroll

Location: Route 6A Dennis (Dennis Village)

Date(s): Sunday, December 8th 12:00 pm – 3:30 pm

Website: Dennis Christmas Stroll 

Details: Stop by local shops along Route 6A for seasonal goodies and a chance to meet the big guy himself with Mrs. Claus. There will be face painting, live music at the gazebo and trolley rides along with plenty of holiday fun along the way!

West Dennis Holiday Stroll

Location: All along Route 28 in Dennis

Date(s): December 14th 11:00 am – 4:00 pm

Website: West Dennis Holiday Stroll

Details: Stop in and see the merchants along Route 28 in Dennis for their West Dennis Holiday Stroll on December 14th for some holiday cheer! There will even be a trolley to take you up and down Main Street.


Eastham Holiday Festival

Location: Orleans-Eastham Elks 10 McKoy Rd & Eastham Gift Barn 4180 State Highway

Date(s): Saturday, December 7th 10:00 am – 1:00 pm

Website: Eastham Holiday Festival

Details: Santa arrives at the Gift Barn at 10:00 am to greet all the boys and girls. There is a free trolley that can take you and the family back and forth between the Eastham Elks Lodge and the Eastham Gift Barn. There will be plenty of crafts, family friendly events and free pizza from the Pizza Barn!


Christmas in Harwich

Location: Throughout the town of Harwich (mainly along Main Street)

Date(s): December 6th – December 8th

Website: Christmas in Harwich 2019

Details: The holiday fun begins on Friday December 6th and continues all weekend long with Christmas caroling, live music, crafts, merchant goody surprises and holiday cheer!


A Seaside Christmas in Orleans

Location: Throughout Orleans

Dates: November 30th to December 30th

Website: A Seaside Christmas in Orleans

Details: Throughout the month long celebration, the town of Orleans hosts a variety of events to celebrate the holidays! Start the holiday fun with a special breakfast with Mrs. Claus on November 30th at the Hole In One or visit with Santa at the Orleans Yacht Club from 8:00 am – 10:00 am. Santa makes a stop at Snow’s Home and Garden between 10:00 am and 12:00 pm before the holiday stroll. Christmas caroling and the stroll will begin at 5:00 pm with tree lighting to follow.


Holly Folly Weekend in Provincetown

Location: Throughout the town of Provincetown (mainly along Commercial Street)

Date(s): Friday December 6th to Monday December 9th

Website: Holly Folly Weekend in Provincetown

Details: There is a variety of family friendly and adults only fun happening December 6th through Monday December 9th in Provincetown celebrating their annual Holly Folly Weekend in Provincetown!


Gardens Aglow: A Treasured Holiday Tradition

Location: Heritage Museums & Gardens 67 Grove Street, Sandwich

Date(s): November 29th – December 29th (Friday, Saturday and Sunday’s)

Website: Gardens Aglow at Heritage Museum & Gardens

Details: Heritage Museum & Garden’s is a wonderland filled with twinkling lights for its annual Gardens Aglow event. Enjoy the family friendly holiday themed activities, displays, music, trains, animals and there will even be a visit from Santa!


Yarmouth Port Christmas Stroll

Location: Route 6A Yarmouth port

Date(s): December 15th 1:00 pm – 4:00 pm

Website: Yarmouth Port Christmas Stroll

Details: The Yarmouth Port Christmas Stroll takes place all along Route 6A in Yarmouth Port. There is a brass band playing all of your holiday favorites, businesses opening their doors to hand out seasonal goodies and Santa can be even found strolling saying hello to little boys and girls along the way! At 4:30 pm on the Village Green there will be caroling and a tree lighting ceremony to finish the Yarmouth Port Christmas Stroll.

Cape Cod Holiday Events & Strolls : Updated for 2019

Get into the holiday spirit this year by checking out these Cape Cod holiday events & strolls. Looking for a warm cup of coffee while you’re out strolling or meeting Santa? Check out our blog, “Cape Cod Coffee Shops Open in the Off Season.” If you’re looking for where to pick up a quick snack on your way to one of these holiday events, our blog “Best Cape Cod Bakeries” has you covered!


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