Cape Cod Activities

Cape Cod National Seashore

With Cape Cod National Seashore less than 15 minutes away from our Chatham hotel, it only makes sense that you will want to spend time exploring what is considered to be one President Kennedy’s greatest legacies. Known locally as simply “The Seashore,” the first site you will reach as you head north (or “down Cape”) from the Chatham Village Highlander Inn is the Fort Hill Area. Once owned by Edward Penniman, a prominent Cape Codder, the Fort Hill Area includes the Penniman family’s original home and large tract of land. A parking lot at the top of the hill overlooks Nauset Inlet and the Atlantic Ocean. A short trail winds around an open field that was originally the Penniman’s farmland. Grab a trail map from the kiosk and extend your hike to include the Red Maple Swamp Trail. Further down Route 6 is the Salt Pond Visitor Center, The Seashore’s largest visitor center. From there you can hike the Nauset Marsh Trail, which winds along Salt Pond and ends at Coast Guard Beach. Other must-sees within Cape Cod National Seashore include the Atlantic White Cedar Swamp Trail in South Wellfleet. From the same parking lot used for the trailhead, you can also check out the Marconi Station Site, with the remains of Guglielmo Marconi’s groundbreaking wireless communication device, and a viewing platform that affords 360-degree views of the ocean and surrounding dune-scape.

Red Maple Swamp
sunrise at Marconi

Whale Watching

With Stellwagen Bank, the busiest summer feeding ground for whales in North America, located less than an hour’s boat ride from Provincetown, it is no surprise that whale watching is one of the most popular things to do on Cape Cod. And with four vessels sailing multiple times per day, it’s also a big business for the Dolphin Fleet, the primary whale watching company in Provincetown. Each of the large vessels is designed specifically for whale watching. Two levels of spacious decks means everyone is virtually guaranteed a rail-side spot. An on-board naturalist provides info on the various whales as they come to view. Humpbacks sightings are common. Watching a humpback doing a full breach, when they leap out of the water, so close that you may well get wet when they plunge back into the water? Anything but common. Finback and minke whales are also frequently spotted, as are dolphins and sea turtles. Trips take between three and four hours; reservations strongly suggested. Each vessel has an onboard snack bar, and restrooms.

Humpback whale

Day-Trip to Provincetown

Even if a whale watch isn’t part of your Cape itinerary, a day-trip to Provincetown is worthy of your precious vacation hours.  Established as an artists’ colony in the 1920s, Provincetown has long celebrated bohemian and alternative lifestyles, and that century-old heritage continues to shine through as an explosion of color and character. Commercial Street is the main drag in town, and it’s where you’ll find much of the action. Shops, galleries, cafes and restaurants line the densely packed one-way street. On a Saturday night in summer, people also pack Commercial Street, in a fun, part-of-the-experience kind of way. Favorite waterfront lunch spots include Fanizzi’s and the Lobster Pot. Should you opt for the Lobster Pot, take your experience to the next level – literally – by requesting a table upstairs where the view is better and the vibe more colorful. Before or after lunch, pop into the Provincetown Art Association and Museum to view collections from famed local artists. Feel like buying a piece of art to remember your trip? There a galleries galore. Feel like getting an adult-only shock to the system? Check out Shop Therapy. Just outside of town are other check-out-worthy attractions including Pilgrim Monument and Cape Cod National Seashore’s Province Lands Visitor Center.

Shop Therapy in Provincetown

Boating Excursions

If you’ve chosen Cape Cod as your vacation destination, it’s likely that spending time on the water is at that the top of your things-to-do-on-Cape-Cod list. Chatham sightseeing tours by boat include seal watches, and a couple of private charter options. Chatham Boat Tours offers charters with a captain for groups of six or fewer. At Nauset Marine East, in East Orleans, you can rent a boat for up to 10 people for a half or full day, and pilot it yourself. This option lets you take in Pleasant Bay and Chatham Harbor at your own pace. Other family-oriented excursions quite close to our Chatham hotel are the Blue Claw Boat Tours, which sails out Nauset Marine East, and Cap’n Kids Fishing Adventures sailing out of Saquatucket Harbor in Harwich Port. For nearby Chatham fishing charters, there is Fish Chatham Charters, Chatham Sport Fishing, and Monomoy Sport Fishing.

stage harbor light from boat

Barnstable Village

If there is a county seat in Massachusetts that’s as charming as Barnstable Village, we have yet to discover it. It’s also one of the oldest villages on the Cape, so the sense of history is incomparable. And it’s close enough to the Chatham Highlander Village Inn that you can take in the town without devoting an entire day to it. Start with lunch at the Dolphin Restaurant on Main Street, and then enjoy a walking tour of the village. Set along Main Street, a.k.a. the Old King’s Highway, are dozens of ogle-worthy historic homes. The old courthouse is a regal stone structure that towers over the surrounding buildings. A couple of doors down is the Barnstable Comedy Club, the oldest and longest-running community theater in the commonwealth. Just outside of the village is the Sturgis Library. Built in 1644, it is the oldest building housing a public library in the country. Once you’ve had your fill of history, head to the nearby harbor for an afternoon sail with Barnstable Harbor Ecotours for a cruise through a saltmarsh. Après-sail cocktails at Mattakeese Wharf, a restaurant that actually sits out over the harbor, are an absolute must. Enjoy an al fresco clam roll at Osterville Fish Too, the clam shack next door, before heading back to the inn.

The Dolphin Restaurant

Select photos courtesy of Kain DeFoe Communications

Chatham Highlander Village Inn