Holiday Strolls & Celebrations on Cape Cod

The view from the top of the ruins of Fort Barrington, Five Islands Village, Antigua.

Author’s Note: A continued Happy Holidays wish to all who are observing one of the 29 holidays that are celebrated by seven of the world’s major religions at this time of year! While it has been a busy 3+ weeks since Thanksgiving, we enjoyed the “happy stress” of hosting Thanksgiving Dinner, partaking in Chatham’s Christmas Stroll, getting off the grid during 9 days to Antigua (a small island in the Lesser Antilles for an overdue vacation) and joining friends on a last-minute ski trip to New Hampshire. A December to remember for sure. 

Apre ski at Loon Mountain to kick-off “snow season.”


As I’ve wrote about previously, I love the seasons and is a big reason why my wife and I have settled in the northeast. The greening of spring, followed by the heat of summer, fall foliage and of course, the much anticipated first snowfall of winter. However, a jolt of 80 degrees and sunshine in December as our trip to Antigua provided, did make me long for a reset to summer…until I strapped on my skis, scanned my Ikon pass, and hit Loon Mountain to open up my “snow season.” I instantly remembered why I love this time of year; the rush of carving a turn on a freshly groomed cruiser (too early in the season for powder), running into old friends in the life line and catching up on the chairlift and of course, all the laughs in the lodge during apre ski complete with apps and local craft drafts. Indeed, winter and the holidays are here, and I’m embracing it! And in a few months, that wonderful feeling of sand between your toes and a warm breeze on your face will be back on my mind.

Holiday Strolls and Celebrations on Cape Cod

The holiday picture from the Whit Tileston Bandstand in Chatham. No bunny hop today.


The weekend of December 7-8 marked Chatham’s Annual Christmas by the Sea Stroll celebration, a time when our family reunites in Chatham for this special holiday and community event. While this weekend event is the official stroll, featuring a tree lighting, breakfast with Santa, historic inn and museum tour, complimentary trolley rides complete with carolers through town, the weekend prior featured Santa’s arrival at the Chatham Fish Pier and a few weeks down the road, Chatham’s First Night will have the town celebration the arrival of the New Year. Indeed, there are a lot of celebratory events and happy people in Chatham in December. The special events are family friendly, but what I appreciate most are the simple things like, the thoughtfully decorated path through Kate Gould park leading to the decorated Chatham Bandstand, the candlelit homes along Stage Harbor Road, and of course, the quiet of walking along deserted beaches. The magic of the season is everywhere.

Morning walks on a deserted beach is one of our favorite activities.

Almost every Cape Cod town has their own holiday celebration/stroll, which are spread throughout mid-November through New Year’s Day (alas, Truro didn’t publicize anything this year), making it possible to celebrate the season multiple times in multiple towns. Local merchants, restaurants and town officials, from all communities have done a great job (whether planned or not) of offering a wide range of family-friendly activities, to historical and cultural events to romantic dinners and everything in between. However, a day on Cape Cod, in my case, Chatham, is not complete without a walk along Ridgevale Beach, no matter the weather.

Barker’s of Orleans has a lot of goodies for our four-legged family members.

As expected, we spent much of our time along Main Street, supporting a few of our favorite small businesses, restaurants and gift shops. My strategy for gift giving is to try and buy local as much as possible/practical by taking pictures of what I initially suspect someone will like, but give myself some time to explore other stores and think about the most thoughtful gift of a bunch of options. In our case, anything dog-related is generally a wiener (pun intended as our dachshund Hana can attest). While Chatham’s Paws & Claws are our favorite groomer, Barker’s in Orleans is a new favorite for treats and toys. 

Buy local.

My holiday survival strategy also includes ducking into my favorite chowder and beer stop, The Squire, to warm up while others continue on their stroll. This particular year, everyone decided to take a well deserved break and chasing the little ones into the game room. 

Regardless have how thirsty or hungry you may be, everyone’s welcome at The Squire!

While the weather never seems to cooperate with a picturesque snowy winter scene, the holiday spirit was in the air (literally, music was playing all around town) and we had a great time catching up, supporting local merchants and dining out. 

The annual “Seaview Street Self-ie” (after The Squire stop of course).

If you find yourself on the Cape this month, do find a holiday celebration to enjoy. There is plenty of spirit in the air!