Take advantage of shoulder season with these 10 mid-Cape must-dos that are just perfect for spring and fall. 

By Lauren Phillips
November 29, 2017
Wequassett Resort and Golf Club on Cape Cod, Massachusetts.
Photo: Courtesy of Wequassett Resort and Golf Club

While there's nothing like a weekend (or week-long) getaway to Cape Cod in the summer, the shoulder seasons of spring and fall offer plenty of great places to eat, drink, and shop, and considerably fewer visitors. Get your off-season Cape on in fine form with these 10 musts.

1. Go for a ride.

Rent a bike from The Orleans Cycle and pick up the 22-mile (and growing!) Cape Cod Rail Trail in nearby Orleans. After a bracing pedal along the former railroad right-of-way, settle in for breakfast at cozy and delicious Hot Chocolate Sparrow.

The charming Main Street of Chatham, Massachusetts, on Cape Cod.
Photo: OlegAlbinsky/Getty Images

2. Stroll Main Street.

Browse and buy along a half-mile stretch of Chatham’s Main Street, with its more than 40 independent galleries, shops, and restaurants. Step inside Ducks In the Window, a rubber-duck emporium home to a spectacular variety of bathtub companions, or The Mayflower, for housewares and gifts with nautical New England style.

3. Take an oyster tour.

Grab a seat on Chatham Shellfish Company’s scow for a tour of its farm on Oyster Pond, where you’ll learn how these bivalves are raised from seedlings to raw bar–ready delights, and enjoy fresh oysters and Champagne afterward.

Watch: A Perfect Weekend in Cape Cod:

4. Drink local beer.

Hog Island Beer Co.’s five core brews, plus seasonal offerings, are ready for tasting in the brewery’s Orleans industrial-chic beer hall (which claims to be the outermost brewery on Cape Cod), where you can sample 5-ounce flights and 16-ounce drafts.

5. Eat local seafood.

Bluefins Sushi & Sake Bar’s spectacular rolls, like the crowd-favorite Red Sox (tuna, crab, cucumber, avocado), feature super fresh seafood—no surprise, considering the proprietor also owns the Chatham Pier Fish Market.

6. Pick up a new book.

Indulge that seasonal need to read at Where the Sidewalk Ends—check the children’s annex for books, toys, story times, and more for the younger crowd—and Yellow Umbrella Books, which stocks an impressive array of books about Cape Cod and its history.

Chatham Lighthouse, Cape Cod
Photo: OlegAlbinsky/Getty

7. Take a wild beach walk.

Start at Chatham Lighthouse Beach, where the eponymous white lighthouse stands guard. Stroll south past seal migration routes and onto a narrow spit of land where you can see Chatham Harbor on one side and the Atlantic on the other.

8. Score a classic beach tunic.

Playing vibrant colors against classic nautical and tropical patterns, MAHI GOLD’s prep-forward resortwear is easily the official uniform of Chatham. Pick up next season’s tunics now.

Thoreau's bar and restaurant at Wequassett Resort and Golf Club
Photo: Courtesy of Wequassett Resort and Golf Club

9. Hit the bars.

One night, get your dive-bar fix at Chatham Squire, which serves up a magnificent burger and a varied drink menu. Spend the next evening amid elevated cocktails and shared plates at Thoreau’s, tucked inside an 18th-century house complete with exposed ceiling timbers and a roaring fireplace.

10. Buy fudge.

It’s not just for kids, is it? Chatham Candy Manor is your childhood beach-vacation sugar flashback with old-school candies, hand-dipped chocolates, and creamy fudges.

Wequassett Resort and Golf Club on Cape Cod
Photo: Courtesy of Wequassett Resort and Golf Club

Where to Stay: Wequassett Resort and Golf Club

Nestled on serene Pleasant Bay (kept as such by a rule banning Jet Skis from the waters), Wequassett Resort and Golf Club sets the bar for Cape hospitality. The only five-star resort in the area, this delightfully rambling assemblage of shingled structures has expansive water views that look good in every season. Rates start at $425.