Being outdoors, breathing fresh air, and enjoying the scenery is what exploring the Cape Cod Rail Trail is all about. Especially from spring through fall (weather permitting during winter), couples and families walk and bike the path. It has become part of Cape Cod culture and an annual tradition for many recreational cyclists. We’ve put together a guide of what to see and do and where to eat along the Cape Cod Rail Trail this year.
Overview of the Rail Trail
If you’re new to this Massachusetts peninsula, you might wonder what is the Cape Cod Rail Trail. It’s a paved path that stretches from Yarmouth to Wellfleet as of 2021. The route is located on a section of what used to be part of the New York, New Haven & Hartford Railroad. The railroad was originally built for freight and passenger trains after the Civil War. However, the passenger service ended in the early 1960s, and the freight service ended in the 1970s.
How long is the trail, you may ask? Currently, it’s 27.6 miles long with plans for expansion. Although it is ambitious, it is possible to bike the Cape Cod Rail Trail in one day. Ideally, you could spend a few days exploring attractions along the route and maybe even swim in some of the freshwater ponds that you’ll pass along the way. Also, the asphalt and mostly flat grade make it easy for all skill levels to cycle and bike the path. It’s even friendly for stroller and wheelchair users. Keep in mind, though, that Orleans and Wellfleet have a few minor grades.
Cape Cod Rail Trail Extension Plans
On the west end of the Rail Trail, there are plans to extend the path through Barnstable to the town line with Sandwich. In addition, there are plans to extend the east end of the route for 2 miles north in Wellfleet.
Starting Your Journey in Yarmouth and Dennis
The best place to start the Rail Trail is in Yarmouth and Dennis. The Yarmouth section of the route is the most recent addition and was completed in spring 2019. On this Cape Cod Rail Trail map, you can see that parking is available on Station Avenue. The path continues west through Peter Homer Park, where there’s additional parking, and currently ends at Higgins Crowell Road. To the east, Cape Cod Rail Trail Dennis parking is available in the Main Street parking lot and at the South Dennis Trailhead on East-West Dennis Road.
There are three bike shops along this section of the route where you can rent and repair cycling equipment. Bike Zone Yarmouth offers road, mountain, and hybrid bicycles as well as cycling gear. Near the South Dennis Trailhead, Barb’s Bike Shop has road and mountain bikes, clothing, accessories, and safety equipment. At the Dennis Cycle Center in South Dennis, you can get road and hybrid bikes, tandem cycles, tricycles, and electric bikes.
Golf enthusiasts can spend some time at Bayberry Hills Golf Course in West Yarmouth, which has three, 9-hole courses with optional championship tees. Bass River Golf Course is a sister location and has an 18-hole layout with small greens and wide fairways. If you park at Peter Homer Park, you can enjoy a variety of activities — softball, soccer, and basketball. It has a playground and food concession too. Additionally, the Indian Lands Conservation Area in South Dennis has a 1.3-mile trail loop with river views.
The Yarmouth-South Dennis section of the route has several restaurants to fuel your adventure. In South Yarmouth, Gerardi’s Cafe makes creative and homestyle Italian cuisine, and Route 28 Diner serves breakfast all day. In South Dennis, Jason’s Tavern serves simple creative dishes — burgers, sandwiches, and fresh seafood — and Red Cottage Restaurant has a diner atmosphere and award-winning breakfast and lunch menus.
Following the Rail Trail Through Harwich and Brewster
As you continue the journey northeast, you’ll pass through Harwich and Brewster. There are several places along this section where you can stop for a picnic and detour to other towns and trails. You’ll find Cape Cod Rail Trail parking on Headwaters Drive in Harwich, on Long Pond Road in Brewster, and at Nickerson State Park in Brewster, which is just down the road from Candleberry Inn.
Along the path are two bike rental shops in Brewster. At Brewster Bike, you can rent road and Trek hybrid bikes, or buy from a full line of bikes and accessories. The Rail Trail Bike & Kayak Shop is located directly on the path, so you can park your car, rent equipment, and start riding straight away.
There are several points of interest along the Harwich-Brewster portion of the route. The William & Barbara Hacker Wildlife Sanctuary is 78 acres of protected land with a 2.75-mile walking trail. For a change of pace, Cranberry Bog Tours in Harwich is the largest organic cranberry bog on the peninsula and offers seasonal tours. At the border of Harwich and Brewster is Long Pond where you can go swimming. Next to the Long Pond Road parking area is Sheep Pond Woodlands, which has walking trails. If you park at Nickerson State Park, consider exploring its 8-mile bike path.
In Harwich, you can stop for pizza, sandwiches, and ice cream at Pleasant Lake Pizza Shark just before you reach Long Pond. The General Store there serves breakfast too. If you wait until you get to Brewster, Stone L’Oven Pizza sits next to the path and serves more than just pizza — pasta, panini, wraps, and sandwiches. Also next to the trail is Guapos Tortilla Shack, which is known for having the best fish tacos.
Continuing the Trek Up to Orleans and Eastham
From Brewster, following the map of the Cape Cod Rail Trail east and north will take you through Orleans and Eastham. If you start the journey in Orleans, there’s only one designated parking lot on Old Colony Way, and it has a vehicle charging station. Eastham doesn’t have designated parking along the route, so keep that in mind while planning your trip.
Despite having fewer parking options between Orleans and Eastham, there are several bike rental options. In Orleans, you’ll find Orleans Cycle with three bike varieties and Mike’s Bike Trail Rentals with equipment for kids and adults. Idle Times Bike Shop has a location in each town and offers full-service rentals. Then, in Eastham, there’s Little Capistrano Bike Shop, which rents and sells new and used bikes.
Many of the points of interest along this route are in Eastham. The Eastham Windmill is the oldest and last working gristmill on the peninsula. The town is home to the Salt Pond Visitor Center for the Cape Cod National Seashore, and it has a museum, theater, and park store. Several trails are nearby — Nauset Marsh, Nauset Bicycle, and Buttonbush Trails.
You can take a breather from biking at Poit’s Lighthouse Mini Golf, which has a full-size, 18-hole course with lighthouses and a winding river. Furthermore, you could tour the restored Nauset Lighthouse.
What Orleans lacks in attractions near the path it certainly makes up for with restaurants. Two favorite Cape Cod Rail Trail restaurants in the town are Nauset Fish & Lobster Pool, which has some of the freshest seafood, and Land Ho!, a charming hangout spot with a variety of food to fuel your journey.
In Eastham, you could stop at Arnold’s Lobster & Clam Bar for a delicious seafood meal, gourmet ice cream, and a quick round of mini-golf, or have pizza, pasta, subs, or burgers at Red Barn Pizza & More.
Finishing Your Rail Trail Cape Cod Adventure in Wellfleet
The final stop on your adventure across Cape Cod is Wellfleet, which rests halfway between the tip and elbow of the eastern side of the peninsula. There are two places where you can park your car if you decide to start the journey from here — the headquarters for the Cape Cod National Seashore on Marconi Site Road and by the Wellfleet Trailhead on Lecount Hollow Road.
You have two options when it comes to Cape Cod Rail Trail bike rental shops in Wellfleet. Both Little Capistrano Bike Shop and Idle Times Bike Shop have locations here and can meet all of your bicycle rental and repair needs.
The main attraction in Wellfleet is the Cape Cod National Seashore. It has 40 miles of ponds, marshes, uplands, and beaches. You can explore wild cranberry bogs, walking and biking trails, and lighthouses throughout the park.
The Block & Tackle is a highly recommended restaurant near the Rail Trail, and it serves a range of smoked meats, sandwiches, fried chicken, and snacks. Alternatively, you can have wonderful seafood at Van Rensselaer’s Restaurant and Raw Bar or French cuisine at PB Boulangerie Bistro.
Where to Pick Up the Cape Cod Rail Trail From Chatham
If you’re visiting Chatham and want to explore the Rail Trail from there, you can get to it via the Old Colony Rail Trail. It’s asphalt-covered and has an easy-to-intermediate difficulty. This path runs west through Harwich, where it connects with the Cape Cod path at the Harwich bicycle rotary. On the other hand, you can always detour to Chatham from the Cape Cod trail. You can see the route on this map.
Where to Stay Near the Cape Cod Rail Trail
You might come across several hotels near the Cape Cod Rail Trail during your journey, but the most central place to stay is Candleberry Inn bed and breakfast in Brewster. Our lodgings are halfway between Yarmouth and Wellfleet and less than 1 mile from the path. We have nine guest rooms, all of which feature luxurious amenities, and a bike rack to park your bicycle, in case you bring your own to the Cape. On top of that, there are more than a dozen Brewster restaurants and things to do in Brewster. We can suggest dozens of other Cape Cod things to do during your stay as well.