Ultimate Winter Guide to Cape Cod

There are two distinctly different types of travelers in this world. The first are the ones that love the carefree vibe of a summer day, traveling to places where the sun always shines, the seas are warm, and flipflops and swimsuits are the only outfit of the day. They love long days and party nights. They swim, they tan, they explore hidden beaches in popular areas and yes, they visit Cape Cod in droves in the summer months, finding everything they love right here on our historic island. But today, we want to talk to the second type of traveler, the ones for whom the nights can never be long enough and the snow can never be deep enough. These travelers declare winter their soulmate and cannot be happy without boots and a colorful parka as they trek through blankets of the white stuff. These romantic souls love the quiet of a dark night as more snow falls softly to the ground, and when they are tucked away under a colorful blanket with a fire roaring in the fireplace and a cup of hot cocoa, coffee, or tea in hand, they are in their element. Our comprehensive winter guide to Cape Cod is designed to enhance your vacation experience to the fullest.

Ultimate Winter Guide to Cape Cod

A Cape Cod vacation in the winter is a far different one than occurs in the summer months, and for those who fear they will have nothing to do in the snowy winter wonderland of the Cape, we at New England Vacation Rentals have created this ultimate winter guide, a day-by-day itinerary, to your vacation in our chilly paradise. And of course, the only thing better than exploring the winter adventures you can have during your stay on Cape Cod will be coming home to our seasonal sanctuaries where warmth, romance, and comfort are awaiting! 

Day 1: Welcome to Your New Happy Place! 

Chances are your first night at the Cape was spent getting to know the comforts of your home sweet vacation home, and perhaps you did nothing more than grab a spicy pie from Pizza Barbone in Hyannis, which happened to be located conveniently near your rental property. There is no wrong way to dive into your first night on Cape Cod, so we hope it was a pleasant one. But today is a new day, and there are a plethora of adventures awaiting you! 

Breakfast is the first item on the agenda, and the Daily Paper is our first recommendation! Offering two locations in Hyannis, 644 West Main and 546 Main Street, this local diner serves breakfast all day, and their breakfasts will definitely stick to your ribs on a cold winter day. After finishing off a delicious Lobster Benedict and a couple of cups of strong, hot coffee, it is time to venture out into the cold (But not that cold, because our Cape is protected from the biggest weather issues and stays relatively warm in comparison to the rest of Massachusetts!) to one of the beaches of Hyannis. A beach in winter? We can almost hear the incredulous tone of your voice as you ask but trust us. While no one is suggesting a swim in the icy waters, the sight of snow-covered sands, gray skies, and stormy waters will reach out and take hold of your winter loving heart! The beaches—East, Kalmus, Sea Street, and Veterans—are a major draw in both winter and summer, and once you experience them, there is no going back. You will be hooked forever, and the pictures you take will offer a stark and rugged beauty that will add warmth to your home when you print and frame them. 

When the need for heat arises, it may be time to head indoors, exploring a little bit of American history at the John F. Kennedy Hyannis Museum. Located at 397 Main Street and open Monday through Saturday from 10 to 5 (These hours can be different over holidays, or on the first Friday of every month, when they stay open until 8 PM for First Fridays events.) Hyannis served as a respite for our nation’s 35th president, serving as a playground and often acknowledged as the summer White House during his term, and this incredible museum delves deeply into his life and his legacy. Ticket prices range from free (for kids 5 and under) to $14 for adults 18 to 64, and a gift shop is filled with items that will serve as concrete reminders of the moments you spent in his favorite part of the world. 

Finally, on this first, fun-filled day of your escape to the Cape, it is time to explore dinner options, which of course should be seafood related. Massachusetts is known for its sweet seafood, and even those who claim not to like it can’t resist a taste, which is why the Black Cat Tavern, located at 165 Ocean Street, is our suggestion for this night’s meal! Offering waterfront views of the harbor and an extensive menu that includes fish, oysters, clams, and so much more, you will want to save room for their Oreo cake as you possibly end your first day with a great meal and live entertainment. 

Day 2: A Tour of Lighthouses 

After a yummy breakfast of Steak Tips and Eggs at Marshland Restaurant, located at 109 MA-6A in Sandwich, (which has made an appearance on everyone’s favorite Food Network show, Diners, Drive Ins, and Dives) you will have all the energy you need for a drive around Cape Cod and a tour of the lighthouses for which we are famous. There are 14 lighthouses on Cape Cod, but not all are easy to access, such as the Sandy Neck Lighthouse in Barnstable, which is actually a private residence and should only be viewed from a distance, perhaps by boat. But never fear; there are many more you can explore! 

The Nauset Lighthouse is the most photographed one on Cape Cod, its red, white, and black structure standing out against the skies in all seasons, perched next to the classic Cape Cod keeper’s house. Located in Eastham and known as one of the Three Sisters, it was completed in 1838 and originally stood about 500 feet away from where it stands now. The Three Sisters, a trio of lighthouses constructed in 1911 after the original threesome fell into the sea, aren’t at water’s edge anymore but are located just a short walk away from Nauset Light, serving as a stately reminder to those early more dangerous days in the seas around Cape Cod. 

Chatham Light is the next structure on our tour, offering a peek at an automated lighthouse still in use. Built in 1877, this pure white structure is much loved, and although they only offer tours in the summer months, a picture taken in front of the lighthouse will make an excellent photo for your annual Christmas card. If you time your travels right, you should stop into the Wild Goose Tavern, 512 Main Street in Chatham, for a bowl of their Spanish Stew, served with your choice of seared cod or scallops! 

Heading back out on the road, Nobska Light in Falmouth is next on the tour. Built in 1829 and offering stunning views of Martha’s Vineyard and Nantucket Sound, this white tower is also still in use, and watching the ferries commute from island to island from the grassy cliff is one of our favorite ways to find peace on a chaotic day. 

With 14 lighthouses on the Cape, we could go on and on about each one, but the best way to learn about these important structures is to visit those you can, including all the ones we listed here, plus others such as Monomoy, Woods End, and Race Point Lighthouses. You won’t be able to tour these beautiful structures during your winter adventures, but just seeing them, photographing them, and enjoying the views from their base will make this winter trip one you will never forget. And in the evening, after being on the road all day, you may wish to just enjoy a dinner at home, and our fully equipped kitchens will make it easy to do just that! 

Day 3: The History of Cape Cod 

Lying just minutes away from the most famous rock in the country, this region is at its heart, practically the birthplace of our country, and as such, winter visitors can enjoy a historic tour of Cape Cod with visits to museums and antique stores, proving once again that education can be entertaining! As with any of our suggestions, travelers can pick and choose their favorite ideas and plan out their own itinerary, but today, we want to step back in time with a tour of museums.  

Breakfast, of course, is where we begin, and today’s pick of the day is for our Chatham guests. The Chatham Filling Station, located at 75 Old Harbor Road, may never have actually been a gas station, but the owners ensure that no one ever leaves hungry, filling their empty stomachs with a delicious array of foods! Preferring cash, but taking debit and credit cards with an additional fee, this locally owned business is worth visiting twice, so why not come back for lunch? 

After the most important meal of the day, the adventures will begin with a visit to the Atwood Museum, located at 347 Stage Harbor Road in Chatham. Built in 1752, over 20 years before our nation fought for its independence, a major renovation project began in 2009, ensuring that it would continue to tell its story for centuries to come. The renovations were done in much of the same ways it was originally constructed, including hand-blown glass windows, ax-hewn beams, and historically correct brick-and-lime mortar was used for restoring the fireplace, ensuring that even the pickiest of architectural buffs will be pleased with the restoration. 

For those who can’t find themselves excited about museums, a visit to Monomoy Salvage Antiques & Gifts will give you a taste of history that you can actually bring home with you! Located at 1134 Main Street in Chatham, you could probably spend the entire day here and not see everything they have to offer, but fortunately, they also offer an online shop that you can peruse from anywhere in the world. 

If you want to continue on with your tour of museums, instead of focusing on just one, some of the best museums on Cape Cod include the Cape Cod Museum of Natural History in Brewster, Highfield Hall and Gardens in Falmouth, the previously mentioned John F. Kennedy Hyannis Museum, and the Mashpee Wampanoag Tribal Museum in Mashpee. The museums we have listed here should be open during your winter visit, but you should check, just in case something changes.  

Day 4: Almost Time to Leave?

We’ve crammed a lot of activities into just three days, so feel free to spread the activities out over your longer stay, but however you choose to explore the winter wonderland that is Cape Cod, we like to suggest that you take at least one day to experience all the comforts of home in our seasonal sanctuaries! Wake up early one morning, bundling up to experience a sunrise on the beaches that are nearest your escape, scramble up some eggs for a hearty breakfast, and then head back to bed for a little midmorning nap. Of course, the sofas in our living rooms are notoriously nap worthy, so maybe you will fall asleep while watching the holiday parade at Thanksgiving on large state-of-the-art televisions. On a snowy day, there is nothing more rewarding than staying in your jammies, sipping coffee or cocoa in front of a roaring fire, reading by the light of lamp placed next to the most comfortable reading chair. After another home-cooked meal, (Our kitchens make cooking fun!) clear the dishes off the table, spread out the pieces of a board game and play late into the night. 

There’s a magic that winter brings to Cape Cod, and our New England Vacation Rentals seasonal sanctuaries reflect that magic. Contact us today to reserve your favorite property today!