Cycling Collection by Jamie S.
Cape Cod Weekend — Exploring the best of the outer and lower Cape
3 days
1-4 h/day
190km
950m
950m
The route begins in Provincetown, winds south through Truro and Wellfleet, continues into Orleans and Brewster, and eventually reaches Chatham before looping back north again. You can either take the 95-minute ferry from Boston (don’t forget to book a bike ticket, too!) or drive up and park in the municipal lot next to MacMillan Pier, which maxes out at $40 per 24 hours. The daily mileage for this route is fairly manageable, and I’ve intentionally spaced out the riding so you can fully enjoy everything along the way—beach walks, seal watching, lighthouse detours, pond dips, and bakery stops. It’s meant to feel like a long weekend rather than a sprint through the Cape.
You can comfortably ride this on a hybrid, gravel, or touring bike, or a Class 1 or 2 e-bike. A road bike works as well, though some sections of the bike paths have some pretty significant root heaves and rougher patches, so slightly wider tires (30mm or more) can make the ride much smoother. Most of the route uses the Cape Cod Rail Trail or paved National Seashore paths, with connecting stretches on quiet back roads. Traffic is generally mild, but shoulder widths vary and you’ll encounter one short section of highway riding on the iconic Route 6 between Truro and Wellfleet that requires extra awareness.
I built the itinerary with overnights in Chatham and Provincetown, and one optional night of camping at Nickerson State Park, set among deep, clear kettle ponds. If you’d rather travel light with just a day pack and a change of clothes, you can easily adapt this into a credit card tour and stick to motels, inns, or Airbnbs in Brewster (where the night of camping is) or Orleans (the next town over). No permits are required, but all lodging—including the Nickerson State Park campsites—books up very, very quickly during the peak summer season, so reserving as early as possible is essential. Late spring and fall are great options for this ride too. The whole Cape is quieter then, and visiting a place like this in the off-season can feel really special, but some restaurants and hotels only open in summertime, so be sure to call ahead.
Expect mild coastal weather (with some windy spots by the ocean), mostly gentle hills (with a few punchy rollers near Truro), endless swimming spots, plenty of seafood shacks and cafés, and no shortage of classic Cape scenery. It’s a relaxed, scenic circuit for all ability levels through some of the best corners of the Cape.
Visibility:
Anyone
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Cape Cod Weekend — Massachusetts
185km
900m
900m
Last updated: December 11, 2025
Do it yourself!
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Activities
80.7km
04:46
400m
390m
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
30.7km
01:48
140m
130m
Easy bike ride. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.
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78.8km
04:35
410m
420m
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
Collection Stats
Activities
3
Distance
190 km
Duration
11:09 h
Elevation
950 m
950 m
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