On Wednesday through Sunday mornings, A Perfect Day In Wellfleet starts with combing the tables at the Wellfleet Drive-In Flea Market (51 Rte. 6, 508-349-0541). Up to 200 vendors hawk collectibles, bric-a-brac, art projects, jewelry, and vintage postcards—and that’s just the first row.
Wellfleet packs a lot of nature into a strip of land only two miles wide. At Mass Audubon’s Wellfleet Bay Wildlife Sanctuary (Rte. 6, 508-349-2615), casual naturalists should follow the Boardwalk Trail over a salt marsh to the tidal flats. Watch for northern harriers cruising the marsh for prey, as well as whimbrels—large brown sandpipers—fattening up for the flight to their South American wintering grounds.
Great Island Trail (Chequesset Neck Rd.) is a more challenging hike on the peninsula—an island until 1831—on the north end of Wellfleet harbor. The trail crosses marsh and woodlands en route to Jeremy’s Point. A side loop leads to the archaeological site of the 18th century pirate hangout, Smith Tavern. Wear good hiking shoes and count on a three-hour round trip.
Twice a day, Lisbeth Chapman offers her Hopper House Tours (508-479-1033) to the houses and landscapes in Wellfleet and Truro that Edward Hopper painted in the early 1930s. The two-hour car ride with entertaining anecdotes covers locations of 31 paintings.
Wellfleet’s best surfing beaches—White Crest Beach (Ocean View Dr.) and Cahoon Hollow Beach (Cahoon Hollow Rd.)—lie at the bottom of 75-foot dunes. White Crest usually has bigger surf and fewer people, but Cahoon Hollow has the Beachcomber (1120 Cahoon Hollow Rd., Wellfleet, 508-349-6055), a rock and roll bar serving fried food and cold beer. Dinner is most fun at Mac’s on the Pier (265 Commercial St., Wellfleet, 508-349-9611) where a basket of oysters goes nicely with an incredibly colorful sunset. If all the tables are taken, plunk down on adjacent Mayo Beach (Kendrick Ave.).
Wellfleet Harbor Actors Theater (2357 Rte. 6, Wellfleet, 508-349-9428), the company known for provocative and often challenging plays, is concluding its summer season with a 2015 play called “Alabama Story” that pits a librarian against a segregationist politician in 1959 Montgomery.