The Best Time to Visit Cape Cod Might Be the Offseason

April 10, 2018

We've partnered with Silvercar, the app-based car rental service featuring premium Audis, to highlight awesome, food-centric weekend and week-long road trips from New York.

When it comes to Cape Cod, the stretch of time from Labor Day to Memorial Day is often treated as a vacation wasteland, when outsiders will only venture up in the event of unseasonably warm October or April weather. As a Boston kid who grew up visiting my grandparents on the Cape year-round, I’ve always felt that the destination’s charms linger long after “the season” has ended. When it’s been once again left to the locals, you get to see a whole, oft-unexplored side to the region.

This is only truer for me now that I’ve settled down in NYC; there’s no better escape from the city crowds than a charming, calming place like the Cape in winter or early spring. So for anyone seeking a getaway of their own, here’s a little run-down of all you can do and see when you’re not being thronged with fellow tourists, plus a few choice places to stop on the drive there and back from New York.

Getting out of the city is easy with Silvercar's pickup locations in Brooklyn and Manhattan. Photo by Matthew Borowick

The drive

The trip from NYC and back presents pit-stop opportunities aplenty. If you’re looking for sights, Newport, Rhode Island is full of them; long the home of some of America’s wealthiest citizens, it offers a rocky coastline with stunning views of both nature’s majesty and human feats of architecture. My favorite hidden attraction in the area, though, is the Green Animals Topiary Garden, America’s very first. The name’s pretty self-explanatory, but it’s still well checking out in person; thankfully, it opens well before full tourist season arrives. 380 Cory's Lane, Portsmouth, RI; 401-847-1000.

Bacon and potato pie at Pepe's in New Haven. Photo by @frankpepepizza

If you’re more utilitarian about your stops, check out the pizza in New Haven, CT. I’ve been told that Modern Apizza is the place to check out. Founded nearly a century ago by a second-generation Italian immigrant, it holds onto its long tradition in a most delicious way. 874 State St., New Haven; 203-776-5306.

Shop the Story

Still hungry? Head to Frank Pepe Pizzeria, another old school favorite—it was founded in 1925—for more. This spot, which was recently featured on Dave Chang's Netflix show Ugly Delicious, is famous for it's white clam pie...but go for whatever moves you, like the bacon and potato pictured above. 157 Wooster Street, New Haven; 203-865-5762.


The Liberty Hill Inn

The Cape is a ninety-minute drive from end to end at the best of times, so when you visit for a long weekend, it’s clever to make your home base somewhere mid-Cape, for easier access to both ends. Try the Liberty Hill Inn in Yarmouth; originally built by shipwrights in 1825, it’ll give you a rustic taste of the Cape’s past and present. Then venture out into the heart of the Cape! 77 Main Street, Yarmouth; 508-362-3976.

Arts Barnstable

My good friend, an artist based in Dennis, gave me the heads up about Arts Barnstable, an organization that promotes all things arts-and-culture from its home base in Hyannis (technically a village within the town of Barnstable)—and a great place to get a sense of the lives and livelihoods of Cape Cod residents. It’s also a good starting point for history buffs, offering a guided tour of Kennedy family history (the family’s vacation home was in Hyannisport). You can do the tour on your own, too, if you’re more an independent spirit. 367 Main Street, Hyannis; 508-862-4990.

The Brewster Store

Nearby Brewster is home to Nickerson State Park, where you'll find an abundance of swimmable ponds and woven through by biking and hiking trails.

My family would camp out there every August—perfect timing to view the Perseid meteor showers—but the trip was never complete without a stop (or three) to get good old saltwater taffy at the Brewster Store, and ice cream at the adjoining Brewster Scoop (black raspberry for me, always). The Scoop only opens closer to the tourist season, but the Store is open year-round. It’s a mid-Cape institution, a true example of the classic Cape Cod general store. 1935 Main Street, Brewster; 508-896-7824.

Old Yarmouth Inn

When you’re ready to dine, check out the Old Yarmouth Inn. It’s got a long and storied history, and I do mean long—it was founded in 1696. Its location almost exactly halfway down the Cape has made it popular among travelers over the centuries since; in fact, they claim you might even run into a ghost while you’re dining there. 223 Route 6A, Yarmouth; 508-362-9962.


Commercial St.

Cape Cod terminology can be a little confusing; the Lower Cape is simply the part of the Cape farthest from mainland Massachusetts. Also known as the Outer Cape, it’s synonymous with gorgeous, rolling sand dunes, but it offers a lot more than just beaches and wildlife refuges.Take Provincetown: No trip to the Cape could be complete without a jaunt to this village located at the very tip of the peninsula. Beautiful seashores, a lighthouse, and a monument to the Pilgrims (who landed here before they found Plymouth) await, as does Commercial St., a stretch bustling with galleries, restaurants, and a general slice of P-town life and LGBT culture.

Provincetown Portuguese Bakery

There's also a long history of Portuguese fishermen in the area, so while you're there, don't miss sampling the Portuguese cuisine; for a quick treat, try the malasadas, or fried dough, and pasteis de natas, which are egg custard tarts, at Provincetown Portuguese Bakery. 299 Commercial St Provincetown; 508-487-1803.

A view of Provincetown Harbour. Photo by Robert Lindsell/ Flickr

Wellfleet Cinemas

On the way back down, you can check out a weekend flea market—or, of course, a flick or two—at Wellfleet Cinemas, a beloved local institution. And if you do happen to be there during or slightly after the season itself, you can catch a double feature at the attached drive-in theater, one of only three remaining in the entirety of Massachusetts. I have a vivid childhood memory of seeing a double feature of Mystery Men and Bowfinger there, not to date myself. 51 State Highway, Route 6, Wellfleet; 508-349-7176.

Chatham Squire

If you’re hungry for more than just theatre concessions, drive down a little bit further to the Chatham Squire in the town of Chatham. One of a handful of restaurants at the elbow of the Cape that stays open during the off-season, the Squire is a popular haunt for locals and a great spot for some good old fried seafood. It’s a great stop on your way back from the outer Cape for a taste of local life. 487 Main St, Chatham; 508-945-0945.


Highfield Hall & Gardens

On your way off the Cape, swing by Falmouth’s Highfield Hall & Gardens: This beautiful 19th-century estate was the site of my friend’s recent wedding, but when it’s not hosting private events it doubles as a cultural center for the Cape. In fact, during my friend’s reception, a few of us were dazzled when we found ourselves wandering into a room featuring a modern art exhibition. The grounds themselves feature more permanent art pieces—and, yes, there are food events too, often showcasing prominent Cape Cod chefs. 56 Highfield Dr., Falmouth; 508-495-1878.

Science Aquarium

At the very Southern tip of Falmouth—a little out of the way, but worth it—is the village of Wood’s Hole, home to the famous oceanographic institution. This intersection of science and the sea gives us the Science Aquarium, a great spot to visit and learn a little bit about the vast waters that have been around you this whole time. 166 Water St., Woods Hole; 508-495-2001.

Pilot House Restaurant and Lounge

Looking for eats? Stop by the Pilot House Restaurant and Lounge, which offers delicious dining with a warm, neighborhood-y vibe, plus one last stunning view overlooking the Cape Cod Canal before you cross it and return home. 14 Gallo Rd., Sandwich; 508 888-8889.

Do you have any favorite road trips from New York? Let us know about them in the comments!

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Gerard Coletta

Written by: Gerard Coletta