The Oregon Trail in Massachusetts: Provincetown

If not for its lack of freshwater, Provincetown (pop. 2, 994), not Plymouth, would be the place we immediately equate with the Pilgrims. Way back in 1620, the band of religious travelers and fortune-seeking shipmates aboard the Mayflower landed here, expecting warm weather (in November, of all times) and good water. Neither was to be found, and the Pilgrims sailed on, disembarking across the bay at Plymouth Rock. Thus, P-town (as natives and in-the-know locals call it) lost its chance to be enshrined as the cornerstone of Anglo-American civilization and has had to butter its bread with something other than the national creation story.

So P-town took to the water. For much of its history, the sea sustained the town, which became a trading spot, whaling village, and fishing port. As those industries tapered off, new ones arose to take their place. Art and tourism now keep P-town busy.

In 1899 Charles Hawthorne opened an art school here, and the town earned the art colony status that persists to this day. Bohemians followed. Among the artists and writers were John Reed, Eugene O’Neill, and George Cram Cook, whose Provincetown Players made theater history. And on the heels of Greenwich Village’s fashionable flock came the car-borne tourists, who have proven themselves as faithful as Capistrano swallows, returning year after year to this tip of the Cape. Provincetown is a particularly strong magnet for East Coast gays and lesbians, so don’t be surprised to see as many rainbow flags as Stars and Stripes waving in the breeze.

That 252-foot tower jutting up over Provincetown is the Pilgrim Monument and Museum (9am-7pm daily May-Aug., daily 9am-5pm daily Apr. and Sept.-Dec., $12), with the best panorama on the Cape: In clear weather the entire peninsula can be seen, as well as the Massachusetts coast at Plymouth.

The summer trade prompts P-town to do its beach-boardwalk strut, as boatloads of day-trippers from Boston mob aptly named Commercial Street each afternoon, tanned couples mingle among the restaurants and outdoor cafés each evening, and fun-seekers fill up the bars and clubs each night. During any other season, however, the beach shuttle becomes a school bus, the wait for a table is negligible, and there’s actually a chance that you’ll find a place to park. Meanwhile, the off-season sunsets are still worth a visit to Race Point or Herring Cove Beach, even if they come at an earlier hour and require extra layers of clothing.

Because Cape Cod juts out into the Atlantic, Provincetown is one of the best spots on the East Coast for whale-watching trips. From April through mid-October, boats of the Dolphin Fleet of Provincetown (800/826-9300 or 508/240-3636) leave many times a day on four-hour trips, traveling out to feeding areas off Stellwagen Bank to see humpback, minke, and finback whales.

Hotels and Restaurants in Provincetown

After a day spent cycling amid dunes speckled with wild roses and beach grasses, or admiring the handiwork of window-box gardeners in P-town’s cottage-lined lanes, you’ll probably get hungry. Snackers may want to try the sugar-coated malasadas from the Portuguese Bakery (299 Commercial St., 508/487-1803). However, if you have a bigger appetite and want a harborside table, consider the moderately priced Lobster Pot (321 Commercial St., 508/487-0842), just east of MacMillan Wharf, for heaping portions of time-tested local favorites such as cioppino or sopa do mar, veggie pastas, and, of course, lobster every which way you want it. It’s open year-round too—an exception in these parts. Enter through the kitchen.

For livelier, less-expensive dining, check out the multicultural menu—one of the few to please vegetarians—at Napi’s (7 Freeman St., 508/487-1145), tucked away behind Tedeschi’s. Spiritus Café & Pizzeria (190 Commercial St., 508/487-2808) is another good low-cost savior, dishing up pizza, ice cream, and lattes to a steady clientele of tattooed young smokers and slackers until 2am on summer weekends.

Planning to spend the night? If it’s a summer weekend, make reservations or you may spend your time searching for a bed rather than basking on the beach. If you don’t mind the occasional bout of late-night laughter from Commercial Street carousers, the Somerset House Inn (378 Commercial St., 800/575-1850 or 508/487-0383, $185 and up) has comfortable rooms and a central location in an old Cape Cod manse. Quieter and calmer, the Inn at Cook Street (7 Cook St., 508/487-3894, $169 and up), in the East End, offers relaxing decks and gardens, and a great breakfast.