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How to Do a Weekend in Chatham, Massachusetts

If you think of Massachusetts’ Cape Cod peninsula as an arm, Chatham is the elbow—the mid-point of the Cape. Chatham’s location is bordered by the Nantucket Sound and Atlantic Ocean, making it home to some of the Bay State’s best beaches. With bike trails, a national wildlife refuge, deserted beaches, and a lively Main Street, Chatham is the perfect place to spend a summer weekend.

How to Do a Weekend in Chatham

Hotel: Chatham Bars Inn has been the epitome of Cape Cod luxury since it opened in 1914. More than a century later, this historical resort is an attraction in its own right, especially after the property’s $100 million renovation was completed in 2015. This oceanfront hotel has a quarter-mile pristine private beach, four of the Cape’s most highly-rated restaurants, and two heated pools. The hotel has over 200 rooms to choose from, including ocean-view cottages and spa suites—adults-only suites that have their own sauna, steam shower, and hydrotherapy tubs.

Friday: Check in to Chatham Bars Inn before sunset, and snag one of the resort’s many Adirondack chairs, perched on a hillside facing the ocean. Order a specialty cocktail from the attentive wait staff and relax your way into vacation mode as you watch the sun set over the sailboats in Chatham Harbor.

After the show, take a short (less than 10-minute) walk into town. Or, take advantage of the Chatham Bars Inn’s free shuttle service—the friendly valets will happily drive you anywhere you need to go in one of the Inn’s fleet of brand new Lexuses. Chatham’s main street has plenty of restaurants to choose from for dinner. For a lively evening, dine at The Squire, a popular tavern that fills up with locals for late-night drinks.

Saturday: After sleeping on a Tempur-Pedic feather mattress and 400-count Frette bed linens, you’re sure to wake up feeling refreshed. Put on your swimsuit, pack a picnic and hop aboard the Bartender, Chatham Bars Inn’s free shuttle (which runs every 30 minutes) to the Outer Beach. The very friendly and knowledgeable Captain John threw in a bonus harbor tour, taking us past the lighthouse and envy-inducing mansions that line the bluffs along the shore. Request the same on your way out or back from the beach.

This isolated barrier beach is only accessible by boat, so you’re likely to have the entire place to yourself. Take a long walk on the fine sand, watch clammers hard at work digging at the shoreline, or just sunbathe and listen to the seals serenade you. The warm waters here attract lots of seals—which in turn attract the Great White Sharks that Chatham has become known for, so keep an eye out!

The waters on the Cape can be chilly, especially at the start of the summer. When you’re ready for a swim you can catch the boat shuttle back to the resort for a dip in the oceanfront heated pool. Or, if you’ve booked one of the Spa Suites, you can warm up with a soak in your own private whirlpool tub, or by sitting in your room’s very own sauna. Spa Suite guests also have access to the resort’s spa pool, an adults-only heated pool and hot tub that’s tucked away at the back of the property, offering a much quieter experience than the main pool.

Once you’ve sufficiently pampered yourself, book a window table at STARS restaurant, where you can admire panoramic views of sailboats bobbing on Pleasant Bay as you dine on ultra-local fresh food sourced from the waters before you and the Chatham Bars Inn Farm, located just down the road. (If you happen to visit STARS summer or early fall 2017, famous Boston chef Jody Adams will be temporarily overseeing the restaurant, making for an even more exciting dining experience.)

Sunday: After the irresistible STARS cuisine you’ll probably be ready for some exercise in the morning. Borrow bikes from the hotel and ride down to Monomoy National Wildlife Refuge. Hike trails that wind through dunes, along freshwater ponds, and beside the ocean. You’ll see plenty of birds, crabs, and other creatures, but hardly any other people.

After, head back to Chatham Bars Inn and pick up a Lexus from the fleet that that the hotel makes available for guests to borrow. Take it for a test drive down to see some of the other fun towns along the Cape.  If there’s no traffic, you could make it to the end of the Cape (Provincetown) in under an hour.

Bars & Restaurants


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Caroline was hosted by Chatham Bars Inn. Follow Caroline’s adventures around Boston and the world on Instagram @TravelWithCaroline and on Twitter @CarolineMorse1.


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