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!

About Cape Cod

About Cape Cod

Having grown up in the northeast, it’s hard to imagine meeting someone who has never been to, let alone heard of, Cape Cod. But alas, it happens. For those who are not familiar with Cape Cod, here is short overview and list of what a visit or vacation may look like, from an admittedly biased observer.

Cape Cod
A satellite view of Cape Cod, MA.

Cape Cod is a peninsula off the southeast coast of Massachusetts jutting out about 67 miles into the Atlantic Ocean. “The Cape” consists of 15 towns beginning at the Cape Cod Canal, two islands (Martha’s Vineyard and Nantucket), and the area around Buzzards Bay. While most people experience Cape Cod during the busy summer months of July and August, the shoulder seasons (spring and fall) are increasingly popular times to visit and even winter is becoming stocked with events and activities to keep people coming back throughout the year. About 200,000 people live on the Cape year round, with the population more than doubling in the summer months.

Well fleet Drive-In
The one and only, Wellfleet Drive-In Theatre.

Cape Cod Rail Trail
The Cape Cod Rail Trail.

While there are many classic Cape Cod traditions to experience such as, watching a double feature at the Wellfleet Drive-In, riding, running or walking the Cape Cod Rail Trail, enjoying the raw bar at The Beachcomber or chowder at The Squire, exploring 63,000 acres of the Cape Cod National Seashore, climbing the steps of the Pilgrim Monument, catching a Cape League Baseball League game at one of ten fields spread from Orleans to Wareham, or  visiting the Kennedy Museum, to name a few (and I didn’t even mention all the festivals and celebrations), these places may not always be there, as we learned painfully with Liam’s due to erosion at Nauset Beach. Take advantage while you can.

Here’s a short list of a few activities that make the Cape, well, the Cape for adults and kids a like:
  • A familiar sight off Route 28 in West Chatham.

    Driving by familiar town and neighborhood sights;

  • Enjoying fresh seafood where ever you turn (if you’re not into that, don’t fret, the Cape is littered with tasty twists on traditional cuisines);
  • Packing up for multiple lazy beach days where you often forget what day it is;
  • Getting dragged with your family on a whale watch only to realize you really enjoyed it, even if you puked;
  • beach toys
    A few of my beach toys.

    Competing with your fellow beachgoers in just about any beach game like paddleball, corn hole, scoop golf, Waboba surf water ball, best sand castle, you name it;

  • Playing the role of wanna be local fisherman or typical tourist for a day of fishing on the boat or clamming in the flats;
  • Boating whether charter or some kind of tour, getting out on the water;
  • Re-discovering your appreciation for a deck of cards, board games and puzzles on rainy days;
  • Realizing soft serve ice cream cannot be beat;
  • Veteran's Field, Home of the Chatham A's
    Veteran’s Field, Home of the Chatham A’s.

    Watching a Cape Cod Baseball League is just about the best way to spend a summer evening on Cape Cod;

  • Treating yourself to something sweet; homemade fudge, salt water taffy and at least one banana split;
  • Building up the nerve to sign-out a sailfish (single) sail boat and not capsize – or drift out to sea;
  • Photographing and touring a few of the dozen or so lighthouses spread throughout the Sound and Bay sides;

    Chatham Lighthouse
    The majestic Chatham Lighthouse on a clear summer day.
  • Finding your inner “Tiger” on the back nine during a competitive game of mini golf;
  • Listening to (my) favorite, Ocean 104.7, custom crafted for Cape Cod’s news and ideas (radio station);
  • Soaking up summer sounds of the town(s) band concerts on summer evenings;
  • Going on breakfast run for fresh brewed local coffee and baked goods, returning as a hero to your family or group of friends;
  • Appreciating nature: beautiful gardens, blooms, sunsets, tides the occasional rainbow;

    A bloom in our backyard.
  • Collecting sea shells, sea glass, and other wash’a shore items; and
  • Cursing yourself repeatedly for deciding to depart the Cape on Sunday after 10:00am (traffic!).
Whatever you decide to do, slow down just a little bit and you will enjoy your time on the Cape.