Chatham (pronounced “Chatt-um”) looks like small-town America the way Norman Rockwell imagined it. Roses climb white picket fences in front of shingled Cape cottages, all within a stone’s throw of the ocean, and there’s a winding Main Street filled with pleasing shops. Pretty as it is, Chatham is one of the Cape’s fanciest towns—and priciest.

If Cape Cod looks like a flexed arm, then Chatham is its elbow, sticking out in the sea. Samuel de Champlain landed here in 1606; in 1656, William Nickerson of Yarmouth built the first house here, next to the wigwam of the local tribal leader. (You’ll still see the name Nickerson all over town.) This is where Nantucket Sound turns into the Atlantic Ocean, and the fishing industry is still active. At the tip of the elbow stands a lighthouse.

Dangling south off the elbow lies Chatham’s natural bonanza: The uninhabited Monomoy Islands, 2,750 acres of brush-covered sand favored by some 285 species of birds migrating along the Atlantic Flyway. Harbor and gray seals are catching on, too: Hundreds now carpet the coastline from late November through May. If you go out during that time, you won’t have any trouble seeing them—they’re practically unavoidable. From Memorial Day to Columbus Day, Outermost Adventures (tel. 508/945-5858) runs boat shuttle service—basically water taxis—to North Monomoy. The ride takes 10 minutes; once on the beach, passengers can walk for 2 minutes to the far side of the spit to see seals gathered along the coast. The shuttle runs every 20 minutes from 8am to 4:30pm; its costs $30 for adults, $25 for kids 12 and under. The boats leave from Outermost Harbor, just south of the lighthouse. Follow signs to Morris Island.

The Beachcomber (tel. 508/945-5265) runs seal-watching cruises out of Chatham Harbor from mid-May to late September daily in season, weekends in the shoulder seasons. Parking is on Crowell Road, at Chatham Boat Company, near the bakery. There are typically four cruises a day—at 10am, noon, 2pm, and 4pm—depending on the weather. The 90-minute cruises cost $34 for adults, $32 for seniors, and $28 for kids 3 to 15, and are free for children 2 and under. Where there are seals, there may also be their main predator, great white sharks. The large number of seals has attracted sharks in recent years, and passengers should stay alert for sightings.