Plan The Ultimate Autumn Cape Cod Adventure With These Luxurious Resorts

Famed for its sprawling sandy beaches, idyllic seaside villages, and wealth of native Bay State wildlife, the eastern Massachusetts region of Cape Cod has become one of New England’s most sought-after summer vacation spots—but there’s a world of opportunity to be discovered during shoulder season as well. Free from the high humidity and large crowds that are present from June to August, autumn is the perfect time of year to plan a trip to this storied peninsula.

As daylight grows short and the Bay State foliage begins its annual turn to crimson, these gorgeous resorts are certain to provide a truly memorable experience that’s a far cry from the dog days of summer.

For Nature Lovers: Ocean Edge Resort

The bayside town of Brewster has earned widespread acclaim for its abundant natural beauty and top-tier accommodations, and for those wishing to experience both firsthand, there’s no better destination than Ocean Edge Resort & Golf Club. Splayed across 429 acres of Cape Cod coast, this massive property perfectly blends modern luxury with old-school Victorian charm, offering two distinct accommodation zones for guests to choose from. While the plush Villages at Ocean Edge serve as the perfect spot for group vacations, the centerpiece of the property is certainly the Mansion. Built at the very beginning of the 1900s, this ornate structure once played home to Cape Cod aristocracy, and offers an equal level of refinement in the modern era.

Guests are welcome to explore its storied halls to brush up on its history or just kick back on their patio with a coffee in hand, but no matter how you choose to spend your stay, be sure to spend a night at Ocean Terrace, a polished open-air dining venue that offers clam chowder, seafood casserole, and a wealth of other tantalizing New England favorites from the sea. Just a few steps away, the abundantly-charming Roscommon Room is the perfect spot for budding bartenders to enroll themselves in a cocktail class, while the basement-level Bayzo’s Pub is home to hearty English-style cuisine, regular live music, and the delicious Bayzo’s Brew, a pale ale produced specifically for the hotel by the peninsula’s long-reigning champion of brewing Cape Cod Beer.

While the Mansion is beautiful in its own right, it’s far from the only splendid sight found nearby. A short walk north of the building, guests can find Ocean Edge’s very own private escape in the form of Bay Pines Beach. During the early hours of the morning, the shore’s abundant tide pools play host to marine hermit crabs, tiny fish, and a wealth of Massachusetts shorebirds, while twilight brings spectacular sunsets best enjoyed with a cocktail in hand at Beach Bar. Those wishing to bask in the beauty of Cape Cod’s stunning fall foliage can grab a rental bike and hit the Cape Cod Rail Trail, or take a cruise over to the iconic Nickerson State Park to stroll alongside one of Cape Cod’s many kettle ponds, while the Cape Cod Museum Of Natural History and Cape Cod Museum of Art are two particularly fascinating institutions to explore west of the property.

For Relaxation: Pelham House Resort

Spanning from the Cape Cod Bay coast to the northern shore of Nantucket Sound, the sprawling settlement of Dennis is home to a particularly diverse array of attractions, with the vibrant Pelham House Resort serving as the perfect base for exploration. During early fall, the property’s massive courtyard outdoor pool is perfect for staving off any lingering heat before the leaves turn crimson, while the nearby private beach is a particularly charming destination for spotting native Cape Cod birdlife. No matter how you spend your day, the grandiose Rooftop is an absolutely essential evening destination, offering top-tier New England seafood, refreshing cocktails, and stellar views of the Dennis Port coast.

Pelham House Resort is an optimal destination for leaving the hustle and bustle of city life, but it’s far from the only escape worth visiting in the area. In the midst of 2022, Pelham House welcomed two new properties across the Cape, both of which offer an experience that’s perfect for family reunions and group vacations. North of the resort, Pelham on Main is equipped with spacious balconies that overlook a massive backyard complete with a saltwater pool, while Pelham on Earle can be found in the neighboring town of Harwich just a couple of steps from the ultra-idyllic Earle Road Beach.

No matter where you end up booking your stay, there’s a wealth of activities to partake in around all three properties. For Pelham on Main and Pelham House Resort visitors, the early days of fall offer ample opportunity to swing by the gorgeous Swan Pond River and kayak to your heart’s content courtesy of Cape Cod Waterways Boat Rentals. Meanwhile, those staying at Pelham on Earle can head north to find First Crush Winery, a charming Harwich outpost that’s known for their refreshing wine slushies.

For Gastronomes: Chatham Inn

While there’s no shortage of top-tier cuisine to be found all throughout Cape Cod, Chatham offers a particularly enticing array of restaurants concentrated in one small community—and the opulent Chatham Inn is home to one of the town’s finest destinations for seasoned gourmands. The only Relais & Châteaux property found on the Cape Cod peninsula, this stunning inn dates back to the 1830s, serving as a prestigious vacation destination for close to two centuries. While the estate is equipped with gorgeous seaside vistas and eighteen cozy guest houses, the crown jewel of Chatham Inn is certainly Cuvée.

A paradise for fine food and wine, this elegant dining venue has earned abundant acclaim for years on end, currently serving as the #1 restaurant in all of Cape Cod according to TripAdvisor. Fans of New England fare will certainly find a wealth of classic dishes served at Cuvée, with each one crafted with a globally-inspired flair courtesy of Executive Chef Isaac Olivo, an alumnus of renowned restaurants including Bourbon Steak and Craft. Whether you decide to spring for the four-course or seven-course menu, each meal is certain to contain a wealth of beloved Bay State ingredients sourced from all across the Cape.

Cuvée may be the culinary gem of Cape Cod, but it’s far from the only restaurant that’s worth visiting in Chatham. Unsurprisingly, seafood reigns supreme across the town, and Impudent Oyster serves as a local favorite for the stuff. Housed in a former church, this long-standing establishment is a haven for scallops, gambas al ajillo, and—of course—oysters, and has also garnered local acclaim for its flavorful cocktails. For those in search of a more casual experience, be sure to head west to find Mac’s Chatham Fish & Lobster, a cozy venue that makes a spectacular plate of fish and chips.