The best biking routes on Cape Cod lead to charming inns, sweet treats, and seaside views. Follow editor Steele Marcoux along a leisurely two-wheel tour.
While you can’t turn back time, you can recapture the days of youth by returning to a familiar place with old friends. That’s what I discovered on a recent Cape Cod biking trip with two of my best friends from college. Today, we live in different corners of the country, and it’s hard to find time to reconnect. So when an opportunity arose to retrace my steps—er, pedals—as a bike-tour leader during college summers, I called my friends and asked them to meet me on the Cape. We dropped everything but our helmets and convened in Provincetown, Massachusetts, where the no-training-required bike rides are more about scenery than sweating.
The itinerary is easier than you’d expect: Over four days, we biked from P’town to Chatham on routes that combined roads and bike trails, sending our luggage ahead in a taxi. Our days felt unhurried as we savored the rejuvenating seaside breezes, coastal scenery bathed in a warm, fall glow, and copious amounts of delicious seafood. (Turns out you work up quite an appetite while biking, even if you’re not Lance Armstrong.) Whether it was the biking, spending quality time with friends, or traveling back to a place wrapped in happy memories, I came home refreshed and energized. If your spirit could use a little recharging, check out my trail notes, call your friends, and head to the Cape.
Start your journey with a day ride around P’town and the surrounding trails, warming up your legs and getting comfortable on your bikes before taking them on the road. This ride is a little shorter than the others, so there is plenty of time for checking out shops, art galleries, and cafés. The highlight is the Province Lands Bike Trail, which winds through woods, traverses dunes, and swings by several beaches. But don’t let the lower mileage fool you: There are hills to climb (and zip back down!), so fuel up with breakfast in town and pack a hearty lunch to enjoy once you reach Race Point Beach. Don’t forget your camera: The trail offers surprising amounts of fall color and some of the most scenic views of Cape Cod National Seashore.
ROUTE: About 8 miles. Follow Commercial Street to Pilgrim Park. Then follow Route 6 until you reach the Province Lands Bike Trail
at Herring Cove. This will take you on a loop out to Race Point Beach and back.
RENT: Ptown Bikes
REST: Rooms at The Red Inn have decks for catching the sunset while sipping a cocktail, and spacious, comfortable accommodations. Plus, you can’t beat the location: right on the harbor and just blocks from Commercial Street shops.
REFUEL: Have breakfast at Wired Puppy coffee shop, grab a picnic lunch from Relish, and stay “home” for a pan-roasted local cod dinner at The Red Inn.
Pack a picnic lunch, and then bid a fond farewell to Provincetown. Send your luggage to Wellfleet in a cab; you’ll be hitting the road for your first long ride. As P’town fades into the distance, Shore Road opens up with sweeping views of the bay dotted with classic New England shingled cottages and vintage motor courts. (Note: Enjoy the flat terrain while it lasts—the hill quotient picks up a bit between Truro and Wellfleet.) Before heading for the hills, stop at Truro Vineyards of Cape Cod for some light wine tasting and the picnic lunch you packed that morning. After Truro, the road merges with Route 6 for a short time, but the shoulders are wide enough for a pack of bicycles, plus there’s a great ice cream store, Savory and Sweet Escapes, to take the edge off the traffic.
ROUTE: About 15 miles. Take Bradford Street out of Provincetown. This turns into Route 6A, then into Shore Road, then back to 6A
before merging with Route 6 for a short period. Take a right on Castle Road, and then turn right on Depot Road. Follow Old
Country Road, then turn right on Coles Neck Road. Take a left on Pole Dike Road, then left onto Main Street, which leads to
the Wellfleet town center.
RENT: Little Capistrano Bike Shop is open Saturdays and Sundays after Labor Day, weather permitting.
REST: You’ll know you’ve arrived at The Holden Inn in Wellfleet when you see the anchors hanging out front. Bonus: The town center and harbor are both within walking distance.
REFUEL: Snag a “rollwich” to go from Box Lunch on your way out of Provincetown; stop for pizza and ice cream—try the pumpkin-gingersnap!—at Savory and Sweet Escapes in Truro; and dive into Mac’s Shack in Wellfleet for fresh lobster, clams, scallops, fish-and-chips, and more of the town’s famous oysters.
The first half of the ride is similar to Day Two, with hilly back roads winding through dense woods. But stay determined: The route eventually opens up to wide ocean views from atop a bluff overlooking LeCount Hollow Beach. When the road brings you back to sea level, take a breather and walk on the beach’s unusually white sand. After the break, pick up the Cape Cod Rail Trail, a 28-mile paved bikeway that follows a former railroad path. Lined with sandwich purveyors and ice cream shops, lots of scenic bridges, and the trip’s best fall foliage yet, the trail offers a tranquil (read: flat and impossible to get lost) alternative to biking along the road.
ROUTE: About 15 miles. Take Commercial Street to Main Street and go right, towards Route 6. Cross Route 6 (on foot) to Cahoon Hollow
Road. Take a right on Ocean View and another right on LeCount Hollow. Turn left onto the Cape Cod Rail Trail; follow it for
9 miles to the Orleans town center.
RENT: Idle Times Bike Shop, Inc.
REST: The Orleans Inn is a lovely Victorian house overlooking Town Cove. Built in 1875 as a sea captain’s mansion, the now-converted inn boasts 11 unique guest rooms, each with big water views, a restaurant, and an occasionally raucous tavern.
REFUEL: Power up with some protein from a specialty omelet at The Bookstore & Restaurant; nosh on subs at Bob’s Sub & Cone (508/349-6181); cool off with ice cream at Emack & Bolio’s when you pull into Orleans; and, because any trip to New England would be incomplete without a visit to a red barn, treat yourself to tasty pizza at The Red Barn in North Eastham.
The last ride is the longest, but take comfort in two facts: One, the all-trail route is mostly flat. Two, there is a big reward waiting in Chatham—the spa at the Chatham Bars Inn. But before you can stretch out for that seaside massage, you have some ground to cover. The Cape Cod Rail Trail leads through the dense foliage of Nickerson State Park, over scenic pond and marsh bridges, and past acres of harvest-ready cranberries. After lunch at the Pleasant Lake General Store, coast into the Chatham town center and check out classic New England shops such as The Mayflower Shop and Puritan Cape Cod. Then treat yourself to one last cone at Buffy’s Ice Cream Shop.
ROUTE: About 18 miles. Follow the Cape Cod Rail Trail from Orleans to the bike rotary (about 11 miles), then pick up the Old Colony
Rail Trail out to Chatham.
RENT: Barb’s Bike Rental
REST: Choose from guest rooms in the Chatham Bars Inn historic main building or in the suite-like accommodations of the oceanfront resort’s newly built cottages. Be sure to book a much-deserved massage at the spa.
REFUEL: In the morning, try donuts from Orleans’ Hole in One; enjoy some roadside sandwiches and country store charm at the Pleasant Lake General Store near Harwich; indulge in some scoops at Buffy’s Ice Cream in Chatham; and head to the Impudent Oyster for one last delicious seafood meal.
A Helmet and Bike Lock: Bring your own, or rent them with your bike.
Comfortable Sneakers: You’ll be doing your fair share of walking when you ditch the bikes to explore Cape Cod’s charming towns and beautiful beaches.
Loose and Comfy Pants: You can skip the spandex, but make sure your shorts or pants are roomy enough for easy pedaling. You can also sport padded bike shorts for optimal comfort, or wear them under your street-casual pants.
A Water Bottle: Make sure you choose one that fits in bike holders. You can find one at any bike store, including the rental places.
Sunglasses: You’ll want them even on cloudy days to protect your eyes and face from UV rays, dirt, dust, and the occasional bug.
Panniers (optional): This bike version of saddlebags is great for stowing extra sunscreen, a camera, and a picnic lunch or snacks. Many bike shops rent them.
Plan Your Trip: Early fall is a great time to see Cape Cod because the quaint shops and cafés are still open, but summer crowds have gone
home. Depending on how late you go, some of the leaves will have turned—but it’ll still be warm enough for barefoot walks
on the beach.
Getting There: Fly to Boston and take the ferry to Provincetown. Once you finish at Chatham, taxi back to P’town to return via ferry.
Taxi Company: Cape Cab Taxi operates in Provincetown, Wellfleet, Orleans, and Chatham and will shuttle your luggage and bikes.
Bike Rentals: Ptown Bikes in Provincetown; Chatham Cycle in Chatham. Try a hybrid—sturdier than a road bike but lighter than a mountain bike—with a cushy seat, and make reservations early; September is a popular month to bike on the Cape.