Don’t sleep on Cape Cod’s winter season. I’ve written extensively on the holiday season and there is certainly no shortage of fun to be had around the holidays (anywhere really).
I’m referring to the cold and gray core winter season, from ‘dry’ January through the beginning of Daylight Savings Time, early March.
As a seasonal destination, Cape Cod (and other seasonal areas) had/s a reputation of ‘being closed for business’ for the winter. Not that long ago, the inside joke was the only buildings open in winter were the post office, grocery store and library. (Probably not too far off.) Similarly, shoulder season marketing is still in its infancy.
It is also hard to blame any business or merchant from giving themselves extended time off during the slowest time of year. The core summer season hustle looks torturous at times.
See, Chatham is open all year long! Photo credit: Jeff Shaw.
But the world is different in 2025, though winter is still winter. Winter on Cape Cod remains quiet. Traffic, practically non-existent, yet there are more people around thanks to a combination of remote work and a growing (albeit at a snail’s pace) year-round population.
Equally noticeable is the landscape. The natural world has transformed into muted tones of brown, gray and dark blue, a vivid contrast to the green of budding bushes or bright colors of annual and perennial plantings. [I intentionally omitted those pesticide infused green lawns…Cape Cod lawns only! If we poison the natural environment that makes Cape Cod so special, what are we left with?]
This is the time to get lost along the fire roads of the Outer Cape. Winter is the time to visit new-to-you beaches for combing, photography or quiet contemplation. Parking is free this time of year. You can probably even bring your dog onto most beaches.
In case you didn’t believe it earlier. Photo credit: Jeff Shaw.
The cold season is an excuse to try new-to-you coffee shops, bakeries or similar delights in all 15 Cape Cod towns. Find those delights.
Sure winter is cold, dreary, and maybe too quiet for comfort. So layer up, wear a hood and push through like our core summer season hustlers. Trust me, it won’t be nearly as torturous.
The lobster trap Christmas Tree in Provincetown. Photo credit: Ptown Tourism.
by Jeff Shaw
The holiday season is upon us! And Cape Cod is a wonderful place to experience authentic Christmas cheer, “where modern amenities and Victorian charm casually coexist.” (Boston Magazine)
So in an effort to spread some Christmas cheer, check out these holiday events on Cape Cod. You may just catch the holiday spirit!
Christmas by the Sea, Chatham
Christmas by the Sea weekend, December 13th – 15th, is full of events that have leapt right out of a Norman Rockwell painting. The celebration kicks off on Friday night with a children’s light parade that escorts Santa down Main Street on a fire truck to the tree lighting ceremony at Sears Park (intersection of Seaview and Main Streets).
Activities continue in shops up and down Main Street as well as free horse & carriage rides and visits with Santa in the Chamber Information booth (next to Yankee Ingenuity gift shop). Saturday brings plenty more events in the businesses around town, including a special movie screening for the little ones at the Chatham Orpheum Theater and Breakfast with Santa.
Christmas Parades, Falmouth, Hyannis & Mashpee
Christmas Carolers in Falmouth. Photo credit: Cape Cod Chamber of Commerce.
Gardens Aglow, Heritage Museum and Gardens, Sandwich
Gardens aglow! Photo credit: Cape Cod Chamber of Commerce.
Gardens Aglow at Heritage Museums & Gardens in Sandwich celebrates the season with over nine miles of holiday lights. Stroll through the illuminated grounds, while also taking time to pose with Santa in a 1914 Ford Model T, take a ride on a vintage carousel, roast marshmallows, and participate in a reindeer scavenger hunt.
Drive through Sandwich and try to spot all of The Giants, over two dozen illuminated sculptures along 6A.
Polar Express, Cape Cod Central Railroad, Bourne & Hyannis
One of Santa’s little helpers. Photo credit: Cape Cod Chamber of Commerce.
All aboard! Magic is in the air on the Cape Cod Central Railroad’s Polar Express, where passengers will sing carol over cookies and hot cocoa. Set to the sounds of the motion picture soundtrack, passengers will relive the magic of the classic story as they are whisked away for a festive trip to meet Santa.
Trains depart out of the Buzzards Bay depot from late November through December.
Lobster Pot [Christmas] Tree, Provincetown
There is quite possibly nothing more quintessential New England than a Christmas Tree made entirely out of lobster traps. Provincetown’s Lobster Pot Tree is made using over 100 of them – all borrowed from local lobstermen – and is accentuated by 3,000+ LED lights and colorful buoys. Visit Provincetown’s Lopes Square anytime during the holiday season.
The renovated bar at the Wild Goose Tavern. Photo credit: Wild Goose Tavern.
by Jeff Shaw
There are numerous ways to see a place. Walking, running, biking, segway, tour bus, taxi, helicopter ride, whatever. An often celebrated, perhaps more likely urban pastime, is the fabled pub crawl.
My personal favorite – perhaps all-time – is the Running of the Santa’s [and Pub Crawl] in downtown Hartford in the mid-2000s. Proceeds raised money for the CT Children’s Medical Center. For a few years, the date was circled on everyone’s calendar and bolstered the season giving with a ton of laughs and shenanigans.
Somehow that brings me back to Chatham, downtown, the fabled Main Street. So here’s an idea for the 21 years old+ crowd, try to see Downtown Chatham [via] Pub Crawl!
Below is a suggested route:
Start
Red Run Bar and Grille bar. Photo credit: Jeff Shaw.
Sure, the restaurant is technically on the outskirts of the rotary, the unofficial start of downtown. But in [summer] season, this place is buzzing with activity, especially during the 22 home games of the Chatham A’s.
The Red Nun porch has a peek-a-boo view of the baseball field. The view would be clear, if not for a row of long standing trees. And don’t get me started about the potential of building out a second floor deck to have an even better view of the field (even with the trees). That porch provides a few high tops, too.
Stop 2
The wall mural at the Chatham Orpheum Theater. Photo credit: Jeff Shaw.
One word: Nonprofit. Two words: Pizza Shark. Three words: Local Nonprofit Theater. More to the point, the cozy little bar and seating area is under the radar. First, the mural. I’ve starred in awe at that masterpiece for years and still see something new each time. With six beers on tap, decent wine list and plenty of cocktails to choose from, the Theater is a great second act [performance pun intended].
Pro Tip: Time your crawl so you can take a break and go see a show!
After undergoing an extensive renovation, the Goose bar is twice as big, so probably twice as fun? A few weeks back, I was late meeting friends, who were seated outside. The inside bartender told me I was not allowed to order a drink at the bar and bring it outside to join them, even though they had closed out their check and were mostly just enjoying the view.
Regardless, the Goose lives inside the Wayside Inn, an iconic hotel in downtown Chatham. Much of the Wayside Inn [rooms] have a view of Kate Gould Park, where band concerts are performed every Friday in the summer as well as Shakespeare in the Park and countless other festivals and events. The back building looks onto Chatham Seaside Links.
Stop 4
The bar at Bluefins Sushi and Sake Bar. Photo credit: Jeff Shaw.
Yes, you read that address right [after re-reading the Wild Goose’s address]. The two restaurants face one another.
Bluefins vibe is way more energetic, though one could argue too much stimulus with the track lighting, techno music, big screen televisions and one of the biggest “U” shaped bars that’s not named The Chatham Squire [well get there in a moment].
Despite the addictive vibe, I still cannot fully forget the former life of the location, Celestino’s, which had a reputation for either over serving or staying open late, or both. For one fateful evening, a few of us popped in there, somewhat shocked it was still open. Almost immediately we watched a young woman drop a slice of pizza onto the floor, step on it, sort of slip on it, then pick it up and eat it. So many years later, I still cannot get that image out of my mind.
I wouldn’t expect anything like that to happen at Bluefins, but hey, “those who don’t know history are destined to repeat it.”
Author’s Note: I never miss an opportunity to tell that story because it was so ridiculous.
End
The fabled Chatham Squire. Photo credit: Jeff Shaw.
Quick disclaimer; there are tons of annual and notable events in each Cape Cod town. This three-part series seeks to highlight one of many notable events that could very easily be swapped in for what follows.
My goal is to actually attend each of these events this year, but as the old adage goes, the more the merrier. I hope to see you there!
“One of the oldest town parades in the United States,” reads the event website homepage. While most people agree the [unofficial] summer season kicks off on Memorial Day Weekend, Fourth of July in Chatham may as well mark the [official] start. The Chatham Fourth of July Parade is an absolute gem of an annual event.
First, the public is encouraged to submit ideas for the annual parade theme to the Parade Committee. Second, best practices to build a “winning float” are actually listed on the website, including a video with five tips! And of course, a baker’s dozen worth of awards are made annually, including most patriotic, funniest, best family entry, best youth entry, etc.
As for onlookers, be sure to place your blanket or chair along the parade route by sunrise on parade day!
It has been a few years, but I had to see for myself what the town of Eastham and turnips have in common. And sure enough, a full gymnasium full of vendors, exhibits and games confirmed the fact that indeed, Eastham is the turnip capital of [the world?!] Cape Cod!
Last year, over thirty local restaurants and food trucks served specials featuring Eastham turnips; soups, sides, entrees and even ice cream! A local celebrity, Bob Seay of GHB News, even delivered the Blessing of the Turnips.
Save the date, August 18, 2024, for the 52nd running of the Falmouth Road Race!
The race website homepage reads: The Falmouth Road Race was established in 1973 and has become one of the premier running events of the summer season.
Each year the race draws an international field of Olympians, elite, and recreational runners out to enjoy the iconic 7-mile seaside course. The creation of the FRR At-Home Edition allows you to experience Falmouth from your hometown. You can walk or run 7 miles in 7 days beginning August 12th.
The nonprofit Falmouth Road Race organization is committed to promoting health and fitness through community programs and philanthropic giving.
Hosted by the Wellfleet Chamber of Commerce, Oysterfest is a two-day, family-friendly festival that celebrates the town’s famous oysters, clams and shellfishing traditions and brings together locals and visitors for a weekend of hometown flavor and fun.
There is something for everyone at OysterFest: local cuisine, a fine art and craft fair, educational lectures, culinary programs, children’s activities, eco-tours, live music, a road race, and the annual Oyster Shuck-Off competition.
For a decade and a half, the Yarmouth Chamber of Commerce has sponsored the annual Yarmouth Sand Sculpture Trail. The trail is one of Yarmouth’s biggest attractions, featuring three dozen or so family-friendly sand sculptures. The trail is usually available for viewing from Memorial Day until mid-October. But beware, some sand sculptures are not completed until mid-June.
Sand sculpture trail maps are available and the public is encouraged to vote for their favorite!
Chatham boasts 60 miles of scenic shoreline, waterways, harbors and ocean open. Unfortunately, access to all that beach is usually limited given privately owned shoreline. Fortunately, designated landings give the public specific areas to access the water (put-in/out).
While I’m working on a more comprehensive project to highlight these areas, below are a handful worth visiting.
Cotchpinicut Landing, 156 Cotchpinicut Road
Let’s start with my favorite, Cotchpinicut Landing, in North Chatham. This quiet neighborhood provides access to an interesting shoreline down a narrow road (looks more like a private driveway). A small parking lot consisting of concrete blocks provides space for a few vehicles. The shoreline is beachcomber’s dream, with plenty of (intact) scallop and oyster shells. Rows of equally spaced pilings are evidence of a former dock and a collection of kayaks, sailboats, and paddleboards rest neatly on dry sand suggest a popular put-in spot. The landing has a great view of Strong Island the barrier beach.
Trailhead to Stage Harbor Point Landing. Photo credit: Jeff Shaw.
Stage Harbor Point, Next to 326 Morris Island Road
A close second in my book is Stage Harbor Point, located off Morris Island Road. This barely visible sandy path snakes through a surprisingly thickly wooded area in the middle of multiple private homes. The path ends with a stunning view of sailboats moored in the calm waters of Stage Harbor. You can walk along the shoreline to the Morris Island Dyke area, popular for clamming and photographs.
Historic marker at Strong Island Landing. Photo credit: Jeff Shaw.
Strong Island Landing, Next to 197 Strong Island Road
The view of Strong Island is obviously good (it is a short paddle away), but the history of the area makes this landing special. Over 100 years ago, it was part of a former World War I United States Naval Airstation. The patrol base was in operation from 1917-1922 and a stone marker located in a grassy area next to the parking lot provides a brief history.
Parking lot of Taylor’s Ponding Landing. Photo credit: Jeff Shaw.
Taylor’s Pond Landing, Across from 37 Taylor’s Pond Road
A South Chatham hidden gem, Taylor’s Pond provides calm waters to start a paddle into Mill Creek (pass Mill Creek Landing) and onto Nantucket Sound. The large parking area gives way to a wooden bridge to put-in your floatation device of choice. A memorial stone bench reinforces the “hidden gem” theme.
Hidden driveway to Vineyard Avenue Landing. Photo credit: Jeff Shaw.
Vineyard Avenue Landing, Next to 238 Vineyard Avenue
Even I didn’t know about Vineyard Landing until noticing a yellow “no beach access” sign on the actual green street sign and pole off Route 28. While it is true there is no beach access, there sure is put-in access to Oyster Pond. The landing also provides a wonderful view of downtown Chatham (most people don’t see downtown from that vantage point) as well as the Chatham Yacht Basin. Even the broken seashell driveway to the landing is mostly hidden behind a set of tall pine trees.
Water Street East Landing stairway and informational sign. Photo credit: Jeff Shaw.
Water Street East, Next to 144 Water Street
The story of this location is shifting sands (erosion) and development (modern day downtown). As the informational sign will explain, Water Street use to be the center of Chatham (in the 1800s), connecting packet ships in Nantucket Sound and related commerce in Mill Pond. When you hear the term Chatham’s “Old Village,” think Water Street and the surrounding neighborhood. Nowadays, the public right of way offers side street parking for a handful of vehicles. A metal staircase brings you down to the sandy shoreline of Lighthouse Beach.
The Port Fortune Landing is also a fun access point. I will explain why through my Chatham Landings Trail project. Stay tuned!
