5 Ways to Cape Cod like a Kennedy
No, we're not sick of celebrating JFK's 100th Birthday. In fact, we can't get enough of the legendary New England family. And while being adopted by this tight clan might not be an option, vacationing like them is. Here's how.
Eat like a Kennedy
Kennedy family gatherings were, and are, synonymous with great food—something matriarch Rose Kennedy took pretty seriously. While roadside clam shacks and soft serve ice cream are Cape Cod musts, the area also has incredible high-end dining. Your inner gourmand will certainly be satisfied time and time again, but still, nothing ever gets too upscale on the hook-shaped peninsula.
Chatham Bars Inn, Chatham
Award-winning chef (and all-around girl boss) Jody Adams is a consulting chef at Stars restaurant at Chatham Bars Inn. She recently got to work creating a special menu with executive chef Anthony Cole that includes a JFK birthday anniversary chicken dish she found (and then updated) in the cookbook In the Kennedy Kitchen, co-authored by Kennedy family chef, Neil Connolly. Connolly served as Rose Kennedy’s private Hyannis Port chef from 1983 to 1995. Cape Cod cuisine is pretty standard, and Chef Adams honored that culinary culture by sticking to the basics (fresh, local ingredients) while adding her signature Mediterranean twist. We can attest to the fact that her Kennedy-inspired roast chicken with basil mashed potatoes, garden tomatoes, and roasted beets is well worth the trip to scenic Chatham.
The royal New England family was all about simple dishes and farm fresh veggies just like this upscale Italian spot in Wellfleet. The laid-back eatery uses as many local and seasonal ingredients as possible when crafting their nightly 7-course tasting menus. Farm-to-table meets modern Italian in dishes like Wellfleet oysters and wild sea beans and beet soup with creme fraiche, garden herbs, and flower petals.
Drink bee-ahs with the locals
Part of Cape Cod’s charm are its many dive bars and casual eateries. Getting dressed up for dinner isn’t really a thing around these parts and sneakers and shorts are almost always acceptable attire.
While the scene here tends to trend on the younger side, slurping frozen drinks and partaking in a poolside dance party are really ageless activities. Enjoy the Hyannis marina views and live music Wednesday through Sunday.
19th Hole Tavern
Cold beers and friendly service are two of the many reasons locals congregate at this Hyannis watering hole. The owner is known to personally welcome newcomers, making everyone and anyone feel like a regular. Shoot some pool and when the late-night munchies kick-in, know there’s a killer grilled hot dog on the menu.
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While there are dozens of salty dives on the Cape, this family-owned business has been an area institution for over sixty years. Pop in for a cold brew or bodacious Bloody Mary along with classic fried clams or fish and chips—both options are worth every calorie consumed. Expect quick and courteous service, moderate pricing, a mix of locals and tourists, and an uber casual vibe (like paper plates and post-meal finger licking casual.) An added plus? They offer boat side service and stunning views of Lewis Bay.
Tour famous JFK hotspots and get an inside look at the lifestyle
The Kennedy Legacy Trail in Hyannis Center
This free, self-guided walking tour hits 10 spots the late president made famous. Begin at the JFK Hyannis Museum and view photo and document archives and more. Get a glimpse inside the family’s summer getaway—the famous Kennedy Compound—via a multimedia exhibit featuring over 80 photographs taken between 1934–1963. Then continue your walk to see the St. Francis Xavier Catholic Church (the summer parish for most of the family), and the Hyannis Armory, where JFK gave his presidential acceptance speech. While you’re in the neighborhood, pop into vintage shop Plush & Plunder to rummage for vintage goods including Jackie-O-worthy baubles, pillbox hats, and large framed sunglasses.
Catch a glimpse of the Kennedy Compound by boat
Sailing was and still is a favorite Kennedy family pastime. Who can’t recall seeing iconic black and white photographs of a handsome JFK and stunning Jacqueline (with her fab sunnies) on a sailboat? Both spent many a summer sailing with their family in Hyannis. The late Senator Ted Kennedy was also an avid sailer and participated in legendary Figawi, racing from Hyannis to Nantucket with his wooden schooner, Mya. The Kennedy boats are moored at Hyannisport Yacht Club, and you can catch a glimpse of them and the compound via private boat charters departing from Bismore Park in Hyannis Harbor. Year-round resident Captain Marcus Sherman and his Catboat "Eventide" will usher you around and explain the local history.
Fully embody JFK at the Cape’s only five-star resort
Wequassett Resort and Golf Club, Chatham, MA
From JFK’s most beloved breakfast dish to all of his favorite summer pastimes, this chic seaside destination offers all of the things that make Cape Cod special. Apparently, JFK was a fan of starting his day with poached eggs and Wequassett’s Twenty-eight Atlantic restaurant serves them on lobster tempura. A little over-the-top, yes, but you’ll burn them off while partaking in the late, great president’s favorite hobbies. Kennedy was a fan of golf, tennis, swimming, and boating—all of which you can participate in at Wequassett along their 27 acres of pristine waterfront on Pleasant Bay.
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