Best Buddies Challenge DIY Routes

We’ve put together some amazing routes should you choose to ride for the Best Buddies Challenge: Hyannis Port! Please wear a helmet, observe the rules of the road, and have fun!

Five Star DIY Route Scale

★ (Novice) – For riders new to cycling – welcome! We think you’ll like it here.

★★ (Beginner) – For riders that have been on a bike in the last few years and are comfortable pedaling for around an hour.

★★★ (Intermediate) – For riders that cycle regularly and are looking for something a bit more challenging than your everyday cruise.

★★★★ (Advanced) – For riders that cycle regularly and understand how to approach different terrains, changing grades, and other cycling challenges.

★★★★★ (Expert) – For the most seasoned of cyclists. Epic climbs and leg-shredding distances await. Don’t forget to smile!

South Shore Routes

1. Route: Craigville to Provincetown 110
Distance: 110.4 Miles
Elevation Gain: 3,297 ft
Difficulty: ★★★★★ (Expert)
https://ridewithgps.com/routes/33846515

Description: This route showcases the “Outer Cape” routes. Riders will start this ride where the Best Buddies Challenge typically ends: Craigville Beach. As riders proceed east the traffic will soften. And the scenery – salt marshes, dunes, beaches, lighthouses, ginger bread houses, marinas, and the cultural kaleidoscope of Provincetown – puts this ride on every New England cyclist’s bucket list. This route also showcases the popular Cape Cod Rail Trail. Be advised, although riders never go higher than 200 feet above sea level, this sandy roller coaster will add up to nearly 3,300 feet of climbing. And with exposure to wind this “flat” route will challenge the fittest of riders.

2. Route: Plymouth, Marion Loop
Distance: 54.6 Miles
Elevation Gain: 2,318 ft
Difficulty: ★★★★ (Advanced)
https://ridewithgps.com/routes/33957175

Description: This is a classic South Shore loop that starts and ends in Plymouth at the Independent Fermentations Brewery. Traveling through Myles Standish State Forest, Best Buddies veterans will recognize the College Pond parking area that hosts a rest stop. This is also the start line for a 7.5 mile Best Buddies Strava segment loop that is woven into this longer ride. Do the loop either on the way out or the way back to tack on a few miles. To the south this route brings riders to a scenic lands end point in Marion before looping back through pine forests and cranberry bogs. Finish with a cold one at the Indy Ferm tasting room, where you might recognize the brewer-in-chief. That’s Paul Nixon, the longtime announcer at Best Buddies who greets every rider at the finish.

3. Route: Wompatuck, Cohasset Loop
Distance: 12.2 Miles
Elevation Gain: 272 ft
Difficulty: ★ – ★★ (Novice – Beginner)
https://ridewithgps.com/routes/33969784

Description: This is a short spin that starts and ends in Wompatuck State Park, site of Rest Stop 1 in the traditional Best Buddies Challenge ride. The ride includes a pleasant spin through the wooded bike path that brings a rider to the classic seaside town of Cohasset. The route includes the most scenic sections of Jerusalem Road, an iconic New England seaside road. Riders will also be completing a Best Buddies Strava segment on this route. While this entire route is relatively short, adding a second loop with a touch more gusto on that segment brings the total distance to about 20 miles. Those seeking more can enjoy a cool down loop in the park or hop into the nearby pump track for some fun with the kids!

North Shore Routes

1. Route: Nahant, Marblehead Loop
Distance: 23.3 Miles
Elevation Gain: 557 ft
Difficulty: ★★ – ★★★ (Beginner – Intermediate)
https://ridewithgps.com/routes/33942615

Description: This circuit has been a long favorite among North Shore roadies who hop out out for an evening roll. Recent improvements in the bicycle infrastructure have now afforded beginners comfortable access to these oceanside vistas all within view of the Boston skyline. Metro residents can either take the train to Lynn or ride the new Northern Strand Rail Trail to make a full day excursion. The mansions and yacht clubs of Marblehead Neck, including the fabled Carcassone on Ocean Drive, the seals off Swampscott, and the amazing Battery 206 gun emplacements on Nahant’s East Point.

2. Route: Beverly, Rockport Loop
Distance: 44.8 Miles
Elevation Gain: 1,669 ft
Difficulty: ★★★ (Intermediate)
https://ridewithgps.com/routes/33969648

Description: This route follows along the MBTA Commuter Rail route, allowing a rider to start or finish this scenic loop any where along the line. Beverly makes a great starting point. We suggest hitting the Atomic Cafe on Cabot Street before rolling north along the ocean. With no major climbs and a wide shoulder, this is a great excursion for an intermediate rider. After passing the fabled Gloucester Fisherman statue, the route turns north. Use due caution through two rotaries and then roll towards Rockport, keeping the ocean to your left. These views afford us a taste of iconic Maine seascapes such as Halibut Point and Pigeon Cove but keep us close to home. There are countless lunch stops to hit in Rockport before rolling back south.

3. Route: North Shore 3-State Century
Distance: 106.3 Miles
Elevation Gain: 3,421 ft
Difficulty: ★★★★★ (Expert)
https://ridewithgps.com/routes/34093763

Description: This three-state route is a glorious exploration of the Merrimack River valley, the Great Bay and reedy shores of the New Hampshire seacoast. This ride starts by rolling right off the MBTA Commuter Rail platform into downtown Newburyport via the Clipper City Rail Trail. From there the route brings us inland along the river before rolling north through the mills of Newmarket and the collegiate villages Dover and Durham. Then the route explores tidal marshes and causeways before crossing briefly into Maine and towards the Atlantic where it turns southward. While the route is dotted with cafes, creameries, general stores and clam shacks, save room for a lunch in Portsmouth or press back towards to Newburyport to make the train home.

Metro West Routes

1. Route: Lexington, Wachusett Loop
Distance: 96.9 Miles
Elevation Gain: 5,330 ft
Difficulty: ★★★★★ (Expert)
https://ridewithgps.com/routes/33942257

Description: This is more of graduation ceremony than a training ride. The profile can appear modest but note the numbers on the left hand side of that graph. At just under 100 miles, this mile-high ride requires one to summit Wachusett Mountain, which lords over the Central Massachusetts highlands. The climbs to the base of the mountain road prove more challenging than the mountain itself. Along the way, however, are classic town centers, orchards, cemeteries and countless historic markers. The redemption, however, is in the return. One gets to descend the mountain like a falcon and take Mountain Road to Princeton Center, from where one can see the Boston skyline on a clear day. This joyful view is not just awesome; it’s inviting. For the rider gets to pedal almost entirely downhill back to Lexington. And the prevailing northwest winds aid a cyclist that much more. Finish this ride and one has stamped a passport for entry into the ranks of a seasoned New England cyclist.

2. Route: Harvard, West Boylston Loop
Distance: 35.9 Miles
Elevation Gain: 1,737 ft
Difficulty: ★★★ – ★★★★ (Intermediate – Advanced)
https://ridewithgps.com/routes/33942089

Description: This route starts and finishes at the Harvard General Store, long a favorite stop for cyclists willing to make the 500 foot climb out of the Boston Basin. But this route takes a rider through the orchards and vineyards of the Central Massachusetts highlands and around the Wachusett Reservoir. After circling back towards the north, riders can follow a path along the western shore of the reservoir, through a railroad cut, over the spillway and down to the base of the Wachusett Dam, which has gathered the waters of the Nashua River for Metro Boston consumption since 1905. Thereafter the route grinds north and back to Harvard for this challenging loop.

3. Route: Concord, Carlisle Loop
Distance: 13.5 Miles
Elevation Gain: 523 ft
Difficulty: ★★ (Beginner)
https://ridewithgps.com/routes/33942128

Description: There may not be a more heavily ridden set of roads in all of New England. These loops were established more than a century ago but became fabled training hills for the likes of John Allis. The meeting spot at Haute Coffee, hidden in an alley of Concord Center, provides an almost clandestine membership to the elite ranks who plan weekday training trysts. From there it is up and over Strawberry Hill and then to stiffer challenge of Cross Street. But the delight of short loop is the Bingham Street descent, with its sweeping left turn that befuddles all but the best riders. Return to Concord along Lowell Road but consider a second lap over Strawberry to set your time on the Best Buddies Strava segment. Or set off for other wonderful explorations to the Sleepy Hollow Cemetery, Walden Pond or the Old North Bridge.