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Cape Cod Holiday Events & Strolls

Updated for 2018!

It’s the most wonderful time of the year. The holiday season is upon us, so share in the magic of the season with your family and friends. Here is our list of where to find all of the Cape Cod Holiday Events & Strolls happening this year.


Pictures with Santa at the Cape Cod Mall

Time: Mall Hours daily through Christmas Eve

Location: The Cape Cod Mall (near the Gap Store), Hyannis


Details: Get your picture taken with Santa at the Cape Cod Mall! Keep an eye on their calendar for special events such as pictures for your pets and Santa.


The Annual Lighting of the Provincetown Monument

Time: 5:00pm – 7:00pm

Location: The Provincetown Monument


Details: To commemorate the first landing place of the Pilgrims on November 11, 1620 the Provincetown Monument is illuminated every year. This event is free.


Gardens Aglow at the Heritage Museum & Gardens

Time: 4:30pm – 8:30pm

Location: Heritage Museum & Gardens 67 Grove Street, Sandwich


Details: The Gardens Aglow at Heritage Museum and Gardens runs from Friday, November 23 to Sunday December 30. From 3:00pm – 4:14pm there is a Santa VIP event which you can buy tickets for in advance.


Lighting of the Lobster Pot Tree in Provincetown

Time: 5:30pm

Location: Lopes Square, Provincetown


Details: Over 100 lobster pots make up this enormous “tree”in Lopes Square, Provincetown.

A Seaside Christmas in Orleans

Time: Depends on the day and activity

Location: Various locations in Orleans


Details: You will find festive events throughout the town of Orleans from November 24 to December 31.


Pet Pictures with Santa at Agway of Cape Cod

Time: 11:00am – 2:00pm

Location: Agway of Cape Cod, 686 Route 134 South Dennis


Details: For $10, you can get your pet’s picture with Santa this year! Please make sure your furry friend is up to date on their vaccinations and on a leash (cash only).


Holly Folly Weekend in Provincetown

Time: Varies throughout the weekend of November 30th – December 2nd

Location: Various locations in Provincetown


Details: There is a little bit of everything during the Holly Folly Weekend in Provincetown! Catch a speedo race downtown and champagne brunch or participate in some shopping and singing Christmas carols by the piano.

Brewster for the Holidays

Time: Varies throughout the weekend of November 30th – December 2nd

Location: Various locations in Brewster


Details: Keep an eye out when in Brewster this weekend for the “Brewster for the Holidays” flag because then you will know that this is where the holiday fun can be found.

Christmas in Harwich

Time: Varies throughout the weekend of November 30th – December 2nd

Location: Center of Harwich


Details: The Christmas in Harwich has Christmas caroling, a tree lighting, carriage rides and the ability to take pictures with Santa.

17th Annual Cape Cod Enchanted Village

Time: 5:00pm

Location: The Cape Codder Resort & Spa, 1225 Iyannough Road Hyannis


Details: Every night from November 30 to December 23, this free and open to the public event features a festive light display, Christmas music and Santa comes by for a visit. Unwrapped gifts and gift cards are collected here and all of the proceeds from this event go to the Independence House.


Hyannis Village Christmas Stroll, Harbor Lighting / Boat Parade and Breakfast with Santa

Time: Throughout the day

Location: Main Street, Hyannis Village


Details: Start your day by having breakfast with Santa before participating in a variety of events throughout the day before the illuminated boat parade in the evening.

Eastham Holiday Festival

Time: Throughout the day

Location: Gift Barn and the Eastham Elk Lodge


Details: From 10:00am to 1:00pm, you can find Santa at the Gift Barn. After your visit with the big guy, take the free trolley to the Elks Lodge for holiday crafts, face painting and tasty treats.

Santa Stampede 5K and Family Fun Run

Time: 9:00am – 12:00pm

Location: The Barley Neck Inn, 5 Beach Road Orleans 


Details: Dress in your holiday best (or costume) for this family fun run! Once the race is complete, the Barley Neck Inn will host the awards for best in race and best holiday costume.

Holiday Festival at Taylor Bray Farm

Time: Saturday December 1st at 9:00am – SundayDecember 2nd at 4:00pm

Location: Taylor Bray Farm, 108 Bray Farm Road Yarmouth Port


Details: Purchase your Christmas tree, holiday swag or other crafts at the Holiday Festival at Taylor Bray Farm. There are plenty of homemade jams and baked goods for purchase as well. 


Yarmouthport Christmas Stroll

Time: 1:00pm – 4:00pm

Location: Route 6A Yarmouthport


Details: Local merchants up and down Yarmouthport Route 6A open their businesses to the public to spread holiday cheer.


Barnstable Village Christmas Stroll

Time: 6:00pm – 8:00pm

Location: Route 6A Barnstable Village


Details: The Barnstable Village Christmas stroll will get you in the holiday spirit with their warm apple cider, holiday goodies and chilled eggnog.


Chatham Christmas Stroll

Time: Friday December 7th  – Saturday December 8th

Location: Main Street Downtown Chatham


Details: The whole weekend will be filled with Holiday fun downtown Chatham. On Friday evening, there will be caroling and a tree lighting to kick it all off.


Wellfleet Holiday Tree Lighting and Sing-Along

Time: 2:00pm – 5:00pm

Location: Wellfleet Preservation Hall


Details: Bring your family and friends to the Wellfleet Holiday Tree Lighting and Sing Along to enjoy some holiday cheer.


Dennis Christmas Stroll

Time: 12:00pm – 4:00pm

Locaton: Route 6A Dennis Village


Details: Live music will be playing throughout the day in the Village Green and there will be trolley rides and hay rides available so that you can check out all of the events going on Route 6A in Dennis.

Cape Cod Holiday Events & Strolls

Enjoy this beautiful time of year with your family and friends and take in the Cape Cod Holiday Events & Strolls. On your way, stop by one of the coffee shops  mentioned in on our “Cape Cod Coffee Shops Open in the Off Season” blog. 

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