The ice cream trucks and lifeguards may be gone, but Cape Cod hardly shuts down after Labor Day. On the contrary, September kicks off what many consider the best time of year to visit this long arm of sand off Massachusetts’s southeastern coast. High-pressure systems bring brilliant blue skies, and traffic finally eases. Meanwhile, the first hints of fall color brighten the salt marsh grasses.
Henry David Thoreau sang the season’s praises when he visited in 1849. “I never saw an autumnal landscape so beautifully painted as this was.” After that initial visit, Thoreau repeatedly returned, walking the entire 62-mile length of the Cape. Fall’s blazing palette is the perfect backdrop for such outdoor pursuits, and the outermost towns of Wellfleet, Truro and Provincetown are ideal for a weekend. They’re all within striking distance of Cape Cod National Seashore’s 44,600 acres of freshwater ponds, sand dunes and surf-pounded beaches.
LAY OF THE LAND
It’s about a three-hour drive from Boston to the tip of the Cape. High-speed passenger ferries from Boston Harbor make the journey in 90 minutes (see listings).
Each of the three towns on Cape Cod’s forearm has its own distinct character. Wellfleet, an 18th-century whaling port, is a refined village of galleries and restored sea-captains’ houses. Oyster boats still work the waters off its lovely natural harbor. (A hugely popular festival honors the beloved bivalve every fall. This year’s OysterFest takes place October 18–19.) The tiny rural community of Truro narrows to a point where only a mile of dunes and moorlands separates the Atlantic from the gentle waters of Cape Cod Bay. Provincetown’s location, at the very tip of the Cape, has helped cultivate a sense of abandon among the artists, writers and nonconformists—and large gay community—who gravitate here. Besides its anything-goes vibe, the town is known for excellent restaurants, stylish inns and indie-designer boutiques.
BY TWO WHEELS
The Outer Cape has miles of bike-friendly back roads and old carriage lanes. But the cycling showpiece is the 22-mile Cape Cod Rail Trail, built on an abandoned 19th-century rail bed. Recently widened, regraded and repaved, the mostly flat trail runs from Dennis to Wellfleet, skirting kettle ponds and cranberry bogs along the way. Parking is free at various trailheads, including the one at LeCount Hollow Road in South Wellfleet. Round-trippers can break for lobster rolls at the landmark Arnold’s Lobster & Clam Bar in Eastham, just off the trail on Route 6 (508-255- 2575). Bike-hauling buses will take you and your wheels back to your car if you’re spent.
For a more challenging, hillier ride, try the Province Lands bicycle trail. It begins in Provincetown at the Province Lands Visitor Center, where an observation deck affords 360-degree views (508-487-1256; open through October). The five-mile loop is almost too busy on summer weekends, but come fall, the roller coaster–like ride through scrubby beech forests and across a moonscape of wind-sculpted dunes is blessedly free of crowds. You can follow spurs off the main trail to the wave-raked Atlantic beaches at Race Point and Herring Cove.
For a mellower inter-dune cruise, great with young kids, pedal the two-mile Head of the Meadow Trail in Truro. (Rent wheels at Provincetown Bikes: 42 Bradford St., Provincetown; 508-487-8735; ptownbikes.com.)
Walking is one of the best ways to discover the subtle pleasures of the Cape; you never know which sand track will lead to Thoreau-worthy moments of inspiration. One of the best places to start rambling is the 1,100-acre Wellfleet Bay Wildlife Sanctuary. This Massachusetts Audubon property is laced with gentle meadows and wooded trails leading to the sandy fringes of bay beaches and freshwater ponds. Bird lovers take note: More than 260 species either live here or stop over in fall en route to warmer climes (508-349-2615; massaudubon.org).
Also in Wellfleet, and part of the Cape Cod National Seashore, is Great Island, connected to the mainland by a narrow causeway. Here a six-mile traverse rewards hikers with views of Wellfleet’s harbor on one side and Cape Cod Bay on the other. The Truro Hills Trail is a 10-mile hike through the stark landscape that inspired painter Edward Hopper. Beginning at Ballstons Beach, it follows old fire roads through fields of bearberry, passes small ponds and ascends to overlooks with sweeping ocean views. The Highland Lighthouse marks the trail’s end. Guides from the Truro Historical Society give tours of the 151-year-old lighthouse, which was moved back 453 feet from its rapidly eroding perch in 1996. Neighboring Highland House, an ad hoc museum of local history, is also worth a visit (508-487-3397; trurohistorical.org; from $3).
PURSUING VERY BIG FISH
Every fall, migrating striped bass and bluefin tuna cruise the waters just offshore, fattening up on Atlantic herring and other baitfish before heading south. “The fish are on the move, and they’re hungry,” says Captain Jeff Smith, owner of Fin Addiction Charters (508-349-1404; finaddiction.com). Striped bass and bluefish can also be landed simply by casting from the shallow surf along the National Seashore. Trout, perch and bass are found in freshwater ponds throughout the Outer Cape.
Fall is also prime time for whalewatching. On any day of the week you can board one of the Dolphin Fleet’s boats in Provincetown harbor and ride to the Stellwagon Bank National Marine Sanctuary, six miles away. Once there, onboard naturalists will help you spot migrating humpback, finback and minke whales, and perhaps the rarer North Atlantic Right whales, in the wild (800-826-9300; whalewatch.com).
PADDLE OR SAIL
The Outer Cape’s freshwater ponds, shallow bay and open ocean provide all kinds of thrills. Eric Gustafson, owner of Funseekers in Wellfleet, gives kiteboarding, surfing and windsurfing lessons through mid-fall (508-349-1429; funseekers.org). “The water is actually much warmer in September than it is in June,” he says, “and there’s a dramatic drop in the number of people around. There’s no better time to come.”
Rent canoes and kayaks from Jack’s Boat Rental, found at the 100-acre Gull Pond and three other locations (508-349-9808; jacksboatrental.com). Flyer’s Boat Rental offers lessons in Rhodes 19 sailboats in the Provincetown harbor (508-487-0898; flyersboats.com). You can be on the move for a weekend—or a whole week—and still not experience everything the Outer Cape has to offer. That’s all the more reason to visit in fall; you won’t have to waste any energy fighting for elbow room.
The fastest way is the 25-minute hop from Boston
via small plane. 800-352-0714; flycapeair.com;
from $92 one way.
Two high-speed ferry companies operate boats
BAY STATE CRUISE COMPANY
from $46 one way
BOSTON HARBOR CRUISES
from $46 one way
The fishing boat and giant lobster on the roof
scream tacky, but the food at this post-and-beam
colonial is sublime. Besides classic clambake fare,
a raw bar serves up the freshest sushi and wild
Wellfleet oysters; the daily specials are
sophisticated takes on local seafood. Eat at
in-the-rough picnic tables, indoors or out.
91 Commercial St., Wellfleet; 508-349-6333;
dinner for two, $40*
An under-the-radar gem. Creative pastas and seafood
star in this cozy, candlelit 18-table dining room
in a classic shingled house. 104 Shore Rd.,
North Truro; 508-487-1019; dinner for two, $80
From a small open kitchen, this diminutive,
romantic 37-seat former fish market in the town’s
East End turns out superb seasonal New American fare.
401½ Commercial St., Provincetown; 508-487-4773;
dinner for two, $90
PATIO AMERICAN GRILL & COCKTAIL BAR
This center-of-town hotspot with a large outdoor
dining area is famous for its black raspberry
mojitos, just-shucked oysters, lobster pot pie
and interesting crowd. 328 Commercial St.,
Provincetown; 508-487-4003; dinner for two, $80
A casual downtown breakfast spot (it stays open
all day) that’s as popular for its homemade granola
and omelets as its great people-watching.
99 Commercial St., Provincetown; 508-487-9639;
breakfast for two, $25
*Prices cover a meal for two, not including drinks,
tax or tip.
RCI-AFFILIATED RESORTS ON CAPE COD INCLUDE:
EASTWOOD AT PROVINCETOWN, Provincetown
SANDCASTLE RESORT, Provincetown
For more information, visit RCI.com or call
STONE LION INN
This 19th-century ship captain’s house-turned-B&B is
within walking distance of town and the harbor.
There are three cheerful rooms with queen-size beds
in the main house, plus an apartment and a three-
bedroom house on the garden-fringed grounds.
130 Commercial St., Wellfleet; 508-349-9565;
stonelioncapecod.com; doubles from $100
A three-room, green-leaning inn within walking
distance of downtown and secluded Dyer Pond.
2118 Old Kings Hwy., Wellfleet; 508-349-6823;
chezsven.com; doubles from $140
BRASS KEY GUESTHOUSE
A gated 42-room compound consisting of nine
historic buildings. Posh extras available in some
rooms include walljetted showers, iPod docks, gas
fireplaces and whirlpool baths. 67 Bradford St.,
Provincetown; 800-842-9858; brasskey.com;
doubles from $110
Directly on placid Cape Cod Bay in the quiet East
End of town, this inn has 10 contemporary light-
filled suites plus kitchenettes and sundecks.
603 Commercial St., Provincetown; 508-487-0165;
watermark-inn.com; doubles from $150