If you think cycling season ends as temperatures go down, think again. When the weather turns chilly on the Cape and the Islands, cycling is one of the best ways to enjoy the cool beauty of fall and winter while staying warm. What are the best trails for off-season cycling? We asked the owners of some popular bike shops to share their recommendations, along with tips on fun things to do after your ride. 

by Alice Lesch Kelly

Melissa Ayala
Little Capistrano Bike Shop
Eastham and Wellfleet


Little Capistrano Bike Shop
30 Salt Pond Road, Eastham (year-round)
1446 Route 6, South Wellfleet (Memorial Day through Columbus Day)
littlecapistranobikeshop.com

When it comes to the bicycle business, the Little Capistrano Bike Shop is all about family. “We’re the sixth generation to own the property, which has been a bike shop for 54 years,” says owner Melissa Ayala. “Currently, three generations work at the shop.” Named after the migrating cliff swallows of San Juan Capistrano in California, the shop rents, sells, and repairs bicycles. 

One of Ayala’s favorite rides is the Nauset National Seashore Trail, which takes cyclists to the Cape Cod National Seashore’s Coast Guard Beach. “This is one of the most beautiful rides in New England,” Ayala says. (Be sure to leave time to check out the National Seashore Center’s walking trails and year-round visitors’ center in Eastham, with its theater, store, and museum.) And don’t miss the Cape Cod Rail Trail (CCRT), a 25-mile trail that follows the path of the former Cape Cod Central Railroad, which ran from the early 1800s to the 1960s. The CCRT takes you through various Cape Cod towns, from South Dennis to Wellfleet. “You’ll pass by marshes, ponds, cranberry bogs, restaurants, and more,” Ayala says. CCRT connects with several other cycling trails and goes through Nickerson State Park, which has biking trails, ponds, and picnic areas. 

Jeff Craddock
Sea Sports Cyclery & Outdoor
Hyannis


Sea Sports Cyclery & Outdoor
1441 Iyannough Road, Hyannis
Open year-round
capecodseasports.com

Born and raised on the Cape, Jeff Craddock has worked at Sea Sports Cyclery & Outdoor in Hyannis since his father, Jim, founded the store in 1993 and has owned it since 2004. Outdoor sports aren’t just Craddock’s business, they’re his passion: In addition to being an elite cyclist, he’s also a kayak and paddleboard instructor and master dive instructor. 

For road biking, Craddock recommends the south (on-Cape) side of the Cape Cod Canal Bikeway. “In the fall, the warm water in the canal can often raise the air temperature a few degrees,” he says. Fall and winter are also an excellent time to ride off-road trails, which can be warmer than open paved trails. “Some people even ride with lights, and as daylight starts to fade, they ride at night in groups off-road,” he says. “It’s more fun to be outside getting fresh air and exercise as opposed to riding a spin bike inside.” He likes the off-road trails around Hathaway’s Pond in Hyannis, the trails in the Old Jail Lane Conservation area in Barnstable, and the Mary Dunn Connector trail in Yarmouth. Cyclists who enjoy sand-riding can take fat-tire bikes for a spin at Sandy Neck Beach in Barnstable or the tidal flats in Dennis. After your ride, Craddock suggests a locally made brew at Cape Cod Beer in Hyannis or dinner at Barnstable Tuscan Cuisine.  

Harvey Young
Young’s Bicycle Shop
Nantucket


Young’s Bicycle Shop
6 Broad Street, Nantucket
Open mid-March to mid-December
youngsbicycleshop.com 

Born and raised on the Cape, Jeff Craddock has worked at Sea Sports Cyclery & Outdoor in Hyannis since his father, Jim, founded the store in 1993 and has owned it since 2004. Outdoor sports aren’t just Craddock’s business, they’re his passion: In addition to being an elite cyclist, he’s also a kayak and paddleboard instructor and master dive instructor. 

For road biking, Craddock recommends the south (on-Cape) side of the Cape Cod Canal Bikeway. “In the fall, the warm water in the canal can often raise the air temperature a few degrees,” he says. Fall and winter are also an excellent time to ride off-road trails, which can be warmer than open paved trails. “Some people even ride with lights, and as daylight starts to fade, they ride at night in groups off-road,” he says. “It’s more fun to be outside getting fresh air and exercise as opposed to riding a spin bike inside.” He likes the off-road trails around Hathaway’s Pond in Hyannis, the trails in the Old Jail Lane Conservation area in Barnstable, and the Mary Dunn Connector trail in Yarmouth. Cyclists who enjoy sand-riding can take fat-tire bikes for a spin at Sandy Neck Beach in Barnstable or the tidal flats in Dennis. After your ride, Craddock suggests a locally made brew at Cape Cod Beer in Hyannis or dinner at Barnstable Tuscan Cuisine.  

Gregg Woodworth
Canal Cruisers Bicycles
Buzzards Bay


Canal Cruisers Bicycles
199 Main Street, Buzzards Bay
Open March to December
facebook.com/CanalCruisersBicycles

Canal Cruisers Bicycles in Buzzards Bay opened in 2009 as a rental shop. “We gradually grew into service and repair, and expanded as time went on,” says owner Gregg Woodworth. Today, Canal Cruisers rents a range of bikes, three-wheelers, trailers, tagalongs, and fishing bikes that are specially designed to carry fishing poles and gear. 

Woodworth points cyclists to the north (off-Cape) side of the Cape Cod Canal Bikeway between the Bourne Bridge and the Sagamore Bridge. “This seven-mile path is always very well maintained by the Army Corps of Engineers,” Woodworth says. “It is a nice scenic, flat, level paved path. Walking, running, rollerblading, and dog walking are also welcome.” For mountain biking, head to the Frances A. Crane Wildlife Management Area in East Falmouth. “If you are an off-road bicyclist, Crane’s Otis 151 Mountain bike trails are a must!” For beach riding, point your fat-tire bike to Scussett Beach in Sagamore. Satisfy your post-ride hunger with a delicious meal at Krua Thai Restaurant, Mahoney’s on Main, or Buzzards Bay House of Pizza.

Phil Hughes
Wheel Happy Bicycle Shop
Martha’s Vineyard


Wheel Happy Bicycle Shop
8 South Water St., Edgartown, Martha’s Vineyard
Open March through November; staff is usually
on call when the shop is closed
wheelhappybicycles.com

RideHAPPY, liveHAPPY, and beHAPPY: That’s the guiding principle at Wheel Happy Bicycle Shop in Edgartown, Martha’s Vineyard. Owner Phil Hughes, with his wife Alleyne, his daughters Madison and Taylor, and his sons-in-law Jesse and Nick, have been running Wheel Happy Bicycle Shop for 18 years. Wheel Happy offers cycle and equipment sales, rentals, and service. 

Hughes’s favorite cool-weather bike ride is the bike path to Oak Bluffs on Beach Road. “On the way to Oak Bluffs you are surrounded by water with Sengekontacket Pond and the Vineyard Sound as you cross over the ‘Jaws bridge’ that is famous from the movie Jaws,” Hughes says. “In Oak Bluffs you roll through the Methodist Campground and its famous gingerbread cottages.” He also likes the ride from South Beach/Katama Beach, with its arresting ocean scenery and views of spectacular homes. “Both rides are doable in the same day, and with so many fine restaurants and inns so close your stay can be quite enjoyable.” Hughes suggests grabbing snacks at the Katama General Store and have a post-cycling cocktail at the Dunes Restaurant in the Winnetu Oceanside Resort. 

Before You Ride

Smart cycling always makes sense, but it’s even more important in chilly weather. Follow these guidelines for a safe, enjoyable ride. 

Dress right

Today’s high-performance cycling apparel can help keep you warm at almost any temperature. 

Equip yourself for safety

Carry trail guides, water, and a charged cell phone. Use reflective gear when visibility is poor, and be sure your bike is in good shape. 

Wear a helmet

Research has found that bike helmets reduce serious head injuries by as much as 60 percent. 

Call ahead

Business schedules may vary due to weather, the pandemic, and other factors. Call to confirm open times. 

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