Exploring Cape Cod by bike: beaches, fresh seafood and classic Americana

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Cape Cod, a huge sandspit sticking out into the Atlantic from the New England coastline, bears an uncanny resemblance to a sailor’s flexed arm. Which is fitting because the cape has a rich maritime history – as well as worldclass beaches, freshwater swimming ponds, historic old towns and some of the best seafood in the country. A three-hour drive from Boston, the cape is a slice of Americana like no other.

The best way to experience it is to take it slow, on two wheels. The Cape Cod Rail Trail runs along a disused railway system built just after the American Civil War. The railways carried freight and passengers between major east coast cities until the great American romance with the automobile blossomed in the 1960s. The railway eventually went bankrupt but the locomotive’s loss was eventually the cyclist’s gain.

The Rail Trail officially opened in 1981 and the 25 smoothly tarmacked miles connect the best bits of the cape, from South Yarmouth to Wellfleet, running through pine forest, salt marshes and cranberry bogs, and joining up some of the best beaches and ponds. It’s mostly flat and easy to navigate (walkers are welcome). Hire a bike right on the trail – try Dennis Cycle Center – and pedal off on an adventure. Start from the town of Dennis, which stretches like a tourniquet across the fullest part of the peninsula’s bicep, from Cape Cod Bay in the north to Nantucket Sound in the south. The Rail Trail, though by no means a major artery, is the lifeblood for two-wheeled travellers.

First stop, craft brewer Devil’s Purse Brewing Co in South Dennis is run by two New Yorkers who now call Cape Cod home. The name? A devil’s purse is the local name for the egg sacs shed by skate, which are often found washed up on beaches. The taproom and beer patio (if you’re in luck you may find a lunchtime food truck) is a short diversion but easy to access from the trail, with cans of Handline Kölsch ready to slip into your rucksack.

Heading west, the trail meanders through grassland and wetland, and you’ll spot what used to be cranberry bogs. Although farmed here since the 1800s, cranberry farming is now in decline. Fortunately some of the prime land you see from the trail has been saved from development by a local conservation group that plans to restore the ecosystem that existed before cultivation.

When you reach the Harwich Bicycle Rotary – a proper UK-style roundabout for bikes – you’ll need to decide: head east to Chatham or go north to Brewster. You can easily do both in a day, so no need to fret about the bike trail less travelled.

It’s here that the Cape Cod Rail Trail joins up with another segment of disused railway, the eight-mile Old Colony Rail Trail, which takes you to Chatham, an affluent, picture book town on the peninsula’s elbow. Before you get to the town centre the trail will take you to the tiny Chatham Municipal Airport. You don’t need to be a plane spotter to enjoy this place. Hangar B is one of the best (and best-kept secret) places to eat on the cape. Open for breakfast and lunch (no reservations), it looks out over the landing strip and has an exciting modern American menu: egg and arancini burrito with truffle, say, or Baja-style fish tacos with pankocrusted haddock.

From here, the rail trail runs roughly parallel north of Chatham’s Main Street, eventually depositing you near the baseball field. Main Street bustles with upscale clothing stores, bookshops and eateries. You’re here for the seafood, so don’t miss out on Mac’s Chatham Fish & Lobster.

Mac’s has five restaurants on the cape and buys most of its fish and seafood direct from local fishers. They also operate Wellfleet Shellfish Company, and the small, firm, sweet and briny oysters from the raw bar are excellent, as are the plump, juicy littleneck clams. And there’s lobster. You can’t come to Cape Cod and not have the full-on steamed lobster dinner with drawn (melted) butter, corn on the cob and coleslaw, and Mac’s is the place to do it. Roll up your sleeves, put that plastic bib on and get messy.

At the other end of Main Street, Buffy’s Ice Cream Café, in a tiny mock-Tudor shop with picnic tables outside, is known for its ice cream bars, which are named after local landmarks. The Chatham Light Bar, two chocolate chip cookies sandwiching chocolate chip cookie dough ice cream, is named after the lighthouse, a local landmark and an active US Coast Guard station.

At the end of Main Street is Shore Road, at the apex of the cape’s elbow, part of the on-road ‘scenic bike route’ loop. Make a left onto Shore Road and you’ll come to Chatham Pier where you can spot seals and watch the fishing boats. Chatham Pier Fish Market sells fresh fish including the cod for which the cape is named (stocks have declined, so cod’s not likely to be local), bluefish, flounder and striped bass. At the takeaway hatch, order New England clam chowder, made with clams, potatoes, bacon and cream – and always pronounced ‘chow-dah’. Lobster rolls come two ways: New England style (served cold in a roll with mayo) and Connecticut-style (in a warmed buttered roll). Being from Connecticut, I recommend the latter. Grab a seat at a picnic bench and enjoy.

Back on Main Street, cycle back along the Old Colony Rail Trail and, at the rotary, follow signs for Brewster. As you head north, the Rail Trail will take you past the lovely old red-painted Pleasant Lake General Store, now also a pizza restaurant that serves cooling scoops of Gifford’s ice cream. Sit on the shady front porch and imagine yourself in a different time.

Back in the saddle, the trail leads through pine and deciduous woods en route to historic Brewster. Settled in 1659, it retains its distinctly old New England feel, with clapboard Cape-style houses and hydrangea-filled front gardens. Just off the trail is Cobies Clam Shack, open since 1948 and a local institution for fried clams and ice cream. To the uninitiated, fried clams can seem puzzling. Do you order the strips (without the clam bellies) or whole-belly clams? Fried food may not be health food but it is delicious. And if you’re going for it, do it right and order the whole clams. Richer and full flavoured they’re a definitive taste of the cape – and Cobies sells some of the best, served with french fries and tartare sauce.

Before your two-wheeled steed needs to return to the bike shop it’s worth one last push (and you’ll want to work off those clams). Heading back towards the rotary, the trail runs past Long Pond, Hinckleys Pond and Seymour Pond, three of the 20 or so kettle ponds on the cape formed by retreating glaciers some 18,000 years ago. Park up at Seymour Pond’s beach to take a long, cooling dip in that clear freshwater. Swim for long enough and you might just get your appetite back.