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.
Three roads – or four, depending on the “mid-town” option described below – and a mere 3.1 miles, showcases much of Chatham’s natural beauty, historic significance and best kept secrets. Those roads: Main Street, Bridge Street, Stage Harbor Road (the fourth, Cross Street) connect to make the Chatham Loop (The Loop).
The Loop is well-known to locals and most summer residents. But everyone who visits Chatham should at least drive The Loop. If time is not an issue, I recommend walking it. While the scenery can be enjoyed by bike or on a run, the slow pace of walking (and controlled breathing; no sweating) will make it much more enjoyable. Any non-motorized approach should provide time to snap pictures, pursue a detour, or take a break without worrying about parking.
The Loop begins at the downtown rotary on Main Street, and runs around the Chatham Lighthouse onto Bridge Street. Bridge Street is the home of Chatham’s only drawbridge, the Mitchell River Bridge, and eventually intersects with Stage Harbor Road, which passes Oyster Pond, ending at the downtown rotary.
Now, if you want to be precise, the shape of The Loop is more of a triangle than the assumed circle. Regardless, it is a quintessential summer outdoor activity for anyone who enjoys the sights and sounds of a beautiful place.
The Chatham Loop (3.1 miles/5K!)
The start of the Chatham Loop. Photo credit: Jeff Shaw.
Main Street (1.2 miles from Downtown Rotary to Chatham Lighthouse)
One could argue there is no better downtown than the Town of Chatham. Sure, Provincetown, Falmouth, Hyannis and Harwich Port receive high marks, too. But Chatham’s downtown is just 0.5 miles and is the home address to many notable locations, including the Chatham Lighthouse, Orpheum Theatre, Eldridge Public Library, Kate Gould Park (home of the Chatham Band and a brand-spanking new engraved brick walkway), Chatham Squire and a range of high- to low-end stories and shops that feature homemade chocolate fudge, locally roasted coffee, colorful ducks, soft serve ice cream and so much more. Within walking distance of Main Street is Veteran’s Field (home of the Chatham A’s of the Cape Cod Baseball League), a 9-hole golf course (Seaside Links), the fabulous Chatham Bars Inn, and the iconic Chatham Fish Pier.
The downtown block ends where Main Street turns right, into the Old Village (a Historic District, beyond and down School Street) and around the Chatham Lighthouse. Monomoy Wildlife Refuge is a short drive from where the road intersects with Bridge Street, at the Chatham Beach and Tennis Club.
Bridge Street (0.8 miles to Lighthouse)
The vast woodlands along Bridge Street. Photo credit: Jeff Shaw.
Bridge Street is a bit of an underappreciated time-warp. A mix of old, historic homes (many proudly displaying preservation awards near their front door) are close to the road as well as mansions (if not compounds) tucked out of sight behind tall vegetation and long driveways.
A vast stretch of woodlands appear, somewhat surprisingly, on both sides of Bridge Street between the residential neighborhood and Mitchell River.
The view from the Bridge Street drawbridge. Photo credit: Jeff Shaw.
As for the drawbridge area, the active harbor will soon be the home of a historic Coast Guard Boathouse. The historic boathouse will be retrofitted for use as a municipal shellfish grow-out facility. The boathouse once served as home base for the famed motor lifeboat CG36500 that participated in one of the Coast Guard’s most heroic rescues, saving 32 crewmen from the stricken tanker SS Pendleton in February of 1952.
Note: If you are up for a short detour, take a left onto Stage Harbor Road from Bridge Street. The road will take you to Stage Harbor Yacht Club, with gorgeous views of the harbor. Nearby is a stone marker honoring Samuel DeChamplain, the first known man to land on these shores (1606), not to mention beautifully restored homes along Champlain Road.
Stage Harbor Road (1.0 miles to Rotary)
The home stretch of the Chatham Loop. Photo credit: Jeff Shaw.
The final stretch of The Loop passes the Atwood House & Museum, home of the Chatham Historical Society. Also, at the intersection of Stage Harbor Road and Cross Street (the “mid-town” route) is a historic schoolhouse, the Atwood School. Finally, the route passes Oyster Pond, a public beach with free parking suitable for families, with moored boats floating with the tide.
“Mid-Town” Route (Cross Street 0.4 miles)
The Midtown Route contains everything above except the views of Oyster Pond. From Stage Harbor Road, turn right onto Cross Street back to downtown (rather than proceeding past Oyster Pond back to the downtown rotary). Along the way is lesser-known Chase Park, home of special outdoor events (commonly arts and craft fairs) and also home to the Chatham Croquet & Lawn Bowling Clubs (and courts), which are free and open to the public when not reserved by the club.
The clubhouse of the Croquet and Lawn Bowling clubs. Photo credit: Jeff Shaw.
Beyond Chase Park is the historic Godfrey Windmill (built in 1791), which is open for viewing every Monday, Wednesday and Friday (11-3) during the summer. Volunteers conduct live demonstrations of making cornmeal. Finally, past the Windmill is the Chatham Labyrinth, which celebrated its 10-year anniversary this year.
Another oddity, which will probably make you smile, across from Shattuck Lane is a home (76 Cross Street), with a replica life-sized “dollhouse” version of the larger home. There is also a life-sized glass blown cow in the backyard.
A ‘whale of an oddity’ can be found in the Old Village. Photo credit: Jeff Shaw.
The iconic Edaville Steam Train in a winter wonderland. Photo credit: Bob Shaw.
By Jeff Shaw
Early Cape Cod vacationers were mostly limited to one way to access the Bay State’s salty outpost and sandy shoreline: trains. It is widely known that railroads opened the West to exploration, settlement, expansion and eventually, statehood. The railroad had a similarly transformative impact on Cape Cod, from sparsely populated farming and fishing villages, to a world renown summer vacation destination. President Grover Cleveland would agree. The railroad, quite literally, put Cape Cod on the map.
Even today, trains remains a secret weapon against the growing congestion of cars, buses and trucks around both Bourne and Sagamore Bridges as well as bustling town centers. To skip traffic jam mayhem, consider riding the rails.
The proof, perhaps legacy is a better word, is the Cape Cod Rail Trail bikeway, which largely follows the old railroad bed that once-upon-a-time connected the Cape Cod Canal all sixty-plus miles to Provincetown, with spur lines to a few communities, such as Chatham and Falmouth.
While the original tracks and trains are long gone, train travel still exists to and on Cape Cod. It’s worth checking out!
The Cape Cod FLYER offers weekend train service from Boston to points southeast to Hyannis from Memorial Day to Labor Day.
CapeFlyer
Operated by the Cape Cod Regional Transit Authority, the CapeFLYER is seasonal, weekend train service from Boston and points southeast. The service runs from Memorial Day weekend through Labor Day weekend from South Station Boston to Hyannis, with stops in Braintree, Brockton, Middleborough/Lakeville, Wareham Village, Buzzards Bay, and Bourne.
Prior to the pandemic, ridership had been growing steadily since the service launched in 2013. It is little wonder why; service includes free Wi-Fi, wheelchair accessibility, pets and bikes ride for free and oh yeah, no Canal-related traffic delays. As a bonus, reservations are never required and extra coaches are also added for holiday weekends.
New in 2022, the train departs a bit later than past service; 5:42pm from Boston arriving in Hyannis at 8:20pm in time to allow passengers to make the last Nantucket ferry, which departs at 8:40pm.
Service begins next week, on Friday, May 27, Memorial Day weekend. Note: On Sunday, May 29, the service will be free to active military and veterans.
Cape Cod Central Railroad offers scenic train rides along 27 miles of rail from West Barnstable to Buzzards Bay!
Cape Cod Central Railroad
The Cape Cod Central Railroad offers scenic train rides across 27 miles of track from Hyannis to Buzzards Bay. The scenic train rides are narrated and programs geared toward a mix of adults, children and/or families.
My better half posing with the Octoberfest spread during a fall scenic train ride. Photo credit: Jeff Shaw
The headlining programs include Cape Cod Dinner Train (fine dining), Sunday Brunch train (family brunch), Polar Express Train Ride (holiday-themed with a visit from Santa Claus). In 2015, an Octoberfest ride was also offered over two weekends. To the surprise of some, Cape Cod has a fall foliage, too!
Edaville Family Theme Park
Just off-Cape in Carver, Edaville Family Theme Park operates a Steam Train. It’s probably been three decades since I’ve been on ‘Engine 5 or 21 or ‘insert number here’, but recall it was nothing short of magical in December, especially with snow on the ground. Indeed, as seven or eight-year-old, I was captivated by the wooden figurines of holiday characters; Frosty the Snowman, reindeer, elves, and of course Santa Claus, lining the snowy woodlands along the tracks.
The author playing conductor prior to riding the Steam Train in a winter wonderland at Edaville, circa 1988. Photo credit: Bob Shaw.
So next time you are mulling a Cape Cod adventure, head to the train station. It feels good to acknowledge Cape Cod’s transportation past, by supporting its railroads of the present and future.
Sharknado made a brief landing in the bushes of the Chatham Village Cafe & Bakery? Photo credit: Jeff Shaw.
Cape Cod towns are often described as charming communities. It is no wonder. Weather-worn shingle cottages, vast coastal landscapes, massive sand dunes, colorful yard plantings, iconic lighthouses, and preserved woodlands, to name a few. Of course, there are the decades-old traditions – parades, bandstand concerts, clambakes, and baseball games. And don’t forget, the outdoor showers, clothes lines, whale watches, white directional signs, beach bonfires and plenty of places where left turns are frowned upon.
Below are a few charming photos of recent Cape Cod days.
Short Drive Home from the Beach
The vehicle is definitely in motion. Notice both hands are on the beach gear, not the vehicle interior. Photo credit: Ellen Shaw.
Usually, this kind of creative “passengering” takes place in the bed of pick-up trucks, but the SUV has gotten in on the fun.
Parking Space Lines are Optional
As a Chatham A’s fan, this disrespect of a parking space is a clear example of the evil associated with the Orleans Firebirds. Photo credit: Jeff Shaw.
Perhaps this driver was a fan of Pirates of the Caribbean. To quote Captain Barbossa, “the (pirate) code [in this case, parking lines] is more what you’d call guidelines than actual rules.”
Charming and Quaint
Chatharbor Pottery on Cockle Cove Road. Photo credit: Jeff Shaw.
One of the more charming and quaint cottages on the Lower Cape, Chatharbor Pottery on Cockle Cove Road is a must-stop when visiting in Chatham.
A Solid Beach Perimeter, Sans COVID Spacing
A beautiful morning at Ridgevale Beach. Photo credit: Jeff Shaw.
Personal space on the beach is always at a premium on summer weekends. Best to arrive early and take note of the high-water mark if you want ample space all day.
Local Art & Inspiration
The unexpected, little joys of an afternoon walk down Chatharbor Lane. Photo credit: Jeff Shaw.
The growing presence of dedicated artist cottages in public spaces is a wonderful trend, yet neighbors are sharing their creativity too!
What charming Cape Cod days have you had recently?
Last spring, when the weather was warming and excitement for summer was brewing, I read an article by Eric Williams, Cape Cod Times, (and one of my favorite Cape media personality) arguing that June is the best month on Cape Cod. Yes, June is one of the best, but I put it in second place. For me, it’s all about September.
Don’t get me wrong, our reasons are nearly identical. The months of June and September:
Avoid the enormous crowds of July and August,
The weather is still warm for outdoor living,
Daylight still lasts until after 7:00 pm and
You don’t have to pay to park at town beaches.
But after “pond-ering” (a nod to Eric Williams kettle pond adventures) a little deeper, I am convinced that September reigns supreme. Whether not you agree, I hope you’ll join me on my quest to K.S.A…keep summer alive!
(1) Seasonal Festivals. Sure, the classic summer outdoor experiences (town band stand concerts, Cape League baseball games and parades) are done for the season, but that just means space is open for fall festivals. Festival events occur every weekend, some run for multiple days and happily continue into the winter. Like, this past weekend was the 13th Annual Doxie Day! How can you beat that?!?
The 13th Annual Cape Cod Doxie Day was held in Barnstable on September 25, 2021. My lovely wife won the Octoberfest raffle prize. Photo credit: Jeff Shaw.
Enough Daylight. No question, June daylight pushes the 9:00 pm envelope and that is fantastic. But September daylight still lasts beyond 7:00 pm, just enough time for 9 holes of after-work golf.
“Lobster-Doxie,” during the costume parade at Cape Cod Doxie Day. Photo credit: Jeff Shaw.
No Crowds. Visiting families with school-aged children, college students and tourists have all returned home. Unless you are going to Mac’s Seafood on a Friday night, you won’t have to worry about crowds or parking this time of year. While staffing shortages certainly pose(d) challenges- and showed the ugly side of inpatient visitors, sadly – businesses (say, restaurants) are well in rhythm by the end of the season.
Who said you can’t swim in September (26) at Cockle Cove Beach, Chatham? Photo credit: Jeff Shaw.
Water Still Warm. The ocean, bay and ponds are still warm, though cooler air will greet you upon your water exit. Need proof? My home base – Ridgevale Beach – and the iconic Snack Bar operates food and sailboat rentals through mid-October.
The Ridgevale Beach, Chatham, salt marsh with Buck’s Creek Bridge in the distance. Photo credit: Jeff Shaw.
Stickerless Beaches – with dogs! Now is the time to visit any beach you ever heard about. All town beaches stop checking for parking passes on Labor Day, and most allow dogs back on the beach in September.
