Cape Cod Rail Trail
Authors: Marco & Angelo

Authors: Marco & Angelo

We own the Candleberry Inn, a boutique bed and breakfast in central Cape Cod. We're glad to share our recommendations on all the great things to explore throughout Cape Cod.

The Ultimate Guide to Exploring the Cape Cod Rail Trail This Year

Table of Contents
    Add a header to begin generating the table of contents
    Scroll to Top

    Exploring the Cape Cod Rail Trail offers immersion in nature with the opportunity to breathe in the fresh air and take in the picturesque surroundings. This experience is particularly delightful from spring to fall but even in winter for those prepared for the weather.

    The rail trail is a staple of the local culture, frequented by couples, families, and cycling enthusiasts as a yearly ritual. To enhance your journey on the trail this year, we’ve crafted a guide detailing the sights, activities, and dining options you can enjoy along the way.

    Get our free Cape Cod Vacation Guide, full of the best things to do in Cape Cod. The best activities, restaurants, museums, events, views, and much more!

    Click here to request the guide.

    Cape Cod Rail Trail Bike Path - Cape Cod Massachusetts
    photo via Friends of the Cape Cod Rail Trail

    Overview of the Cape Cod Rail Trail

    If you’re unfamiliar with this charming region of Massachusetts, you might be curious about the Cape Cod Rail Trail. This well-maintained, paved pathway extends over 27.5 miles from Yarmouth to Wellfleet. The trail’s asphalt surface and mostly flat terrain make it accessible for cyclists of all abilities, including those with strollers and wheelchairs. Just note that there are some slight inclines, particularly in Orleans and Wellfleet.

    Rail Trail History

    The trail occupies a historic corridor once served by the New York, New Haven & Hartford Railroad, which was constructed post-Civil War to carry both freight and passenger traffic. Passenger services on this line ceased in the early 1960s, followed by the discontinuation of freight services in the 1970s.

    Riding the Path

    While it’s a bit of a challenge, it’s feasible to cycle the entire Cape Cod Rail Trail in a single day. To appreciate the scenic vistas and local attractions, though, you can take a few days to explore the trail. Along the way, you might even enjoy a dip in the numerous freshwater ponds dotting the landscape.

    Cape Cod Rail Trail Extension Plans

    Plans are in motion to lengthen the rail trail westward through Barnstable and up to Sandwich. Similarly, there is an initiative to push the east end of the route an additional 2 miles north in Wellfleet.

    Indian Lands Conservation Area - Cape Cod Trail Rail
    Indian Lands Conservation Area | photo via Thomas L

    Starting Your Journey in Yarmouth and Dennis

    A great starting point for the rail trail is between Yarmouth and Dennis. Finished in spring 2019, the Yarmouth segment is the newest extension. The Cape Cod Rail Trail has available parking on Station Avenue. From there, the trail proceeds westward, passing through Peter Homer Park where you’ll find additional parking and concluding at Higgins Crowell Road. Heading eastward, you can find parking in Dennis at the Main Street parking lot and the South Dennis Trailhead on East-West Dennis Road.

    Bike Rentals

    Along this stretch of the trail, cyclists have access to three bike shops for rentals and repairs. Bike Zone Yarmouth provides a selection of road, mountain, and hybrid bikes in addition to various cycling accessories. Close to the South Dennis Trailhead, Barb’s Bike Shop offers a range of road and mountain bikes, apparel, accessories, and protective gear. Meanwhile, Dennis Cycle Center in South Dennis has road and hybrid, tandem, and electric bicycles and tricycles for a diverse biking experience.

    Nearby Attractions

    Golf lovers have the opportunity to enjoy three courses while riding the trail — The Winds at Bayberry Hills championship course, The Links at Bayberry Hills, and Bass River Golf Course — all of which are part of Yarmouth Golf. For those parking at Peter Homer Park, a host of recreational activities awaits — including softball, soccer, and basketball — along with a playground for the kids and a spot to grab a bite to eat. Moreover, the Indian Lands Conservation Area in South Dennis provides a scenic 1.3-mile trail loop with picturesque river vistas.

    Restaurants

    The stretch of the route between Yarmouth and South Dennis boasts a variety of dining options to complement your journey. In South Yarmouth, you can savor the inventive and traditional Italian dishes at Gerardi’s Cafe. Moving on to South Dennis, Jason’s Tavern features a menu of straightforward yet imaginative fare, including burgers, sandwiches, and fresh seafood. Additionally, the Red Cottage Restaurant delivers a classic diner experience with its award-winning breakfast and lunch offerings.

    Nickerson State Park - Cape Cod Trail Rail
    Nickerson State Park | photo via Bill M

    Following the Rail Trail Through Harwich and Brewster

    Traveling northeastward on the trail, you’ll traverse the towns of Harwich and Brewster. This segment offers numerous spots perfect for leisurely picnics and opportunities to explore adjacent towns and connecting trails. Convenient parking for the Cape Cod Rail Trail is available on Headwaters Drive in Harwich and on Long Pond Road in Brewster. Additionally, you can park at Nickerson State Park in Brewster, which is a short distance from the Candleberry Inn.

    Bike Rentals

    Two bicycle rental shops are conveniently situated along the trail in Brewster. Brewster Bike offers a selection of road and Trek hybrid bikes for rent and sells a comprehensive range of bicycles and related accessories. Additionally, Rail Trail Bike & Kayak Shop is positioned right on the trail, allowing you to easily park your vehicle, rent the necessary gear, and embark on your ride without delay.

    Nearby Attractions

    The Harwich-Brewster section of the trail features a variety of attractions. The William & Barbara Hacker Wildlife Sanctuary spans 78 acres and offers a 2.75-mile trail for walking amidst protected landscapes. For an educational excursion, consider visiting Cranberry Bog Tours in Harwich, which is recognized as the largest organic cranberry bog on the Cape and provides seasonal guided tours.

    At the juncture of Harwich and Brewster lies Long Pond, a perfect spot for a refreshing swim. Adjacent to the parking area on Long Pond Road, you’ll find Sheep Pond Woodlands, featuring its own network of tranquil walking trails. Moreover, if you choose to park at Nickerson State Park, you have the option to explore its 8-mile bike path.

    Restaurants

    In Harwich, before arriving at Long Pond, you have the option to grab pizza, sandwiches, and ice cream at Pleasant Lake Pizza Shark, which also offers breakfast at the adjacent General Store. Alternatively, if you continue on to Brewster, Stone L’Oven Pizza Co. is conveniently located next to the trail and offers a diverse menu that includes not only pizza but also pasta, panini, wraps, and sandwiches.

    Get our free Cape Cod Vacation Guide, full of the best things to do in Cape Cod. The best activities, restaurants, museums, events, views, and much more!

    Click here to request the guide.

    Nauset Lighthouse - Cape Cod Rail Trail
    Orleans and Eastham | photo via Bev B

    Continuing the Trek Up to Orleans and Eastham

    Navigating the Cape Cod Rail Trail from Brewster in an eastward and northward direction, you will pass through the towns of Orleans and Eastham. Starting from Orleans, you’ll find a single designated parking area located on Old Colony Way, which is equipped with a vehicle charging station. In contrast, Eastham lacks designated parking facilities directly on the trail, so it’s important to consider this when organizing your excursion.

    Bike Rentals

    Although parking may be limited between Orleans and Eastham, cyclists have access to a number of bike rental services. In Orleans, Orleans Cycle provides a selection of three types of bikes, while Mike’s Bike Trail Rentals caters to both kids and adults. With locations in both towns, Idle Times Bike Shop offers comprehensive rental services. Moving on to Eastham, The Little Capistrano Bike Shop is available for those looking to rent or purchase new and pre-owned bicycles.

    Nearby Attractions

    Eastham is a treasure trove of attractions along the trail. The Eastham Windmill is a historic gem, recognized as the oldest functioning gristmill on Cape Cod. The town also boasts the Salt Pond Visitor Center, which serves as the main hub for the Cape Cod National Seashore and features a museum, theater, and store. For those looking to explore nature trails, the Nauset Marsh, Nauset Bicycle, and Buttonbush Trails are all in close proximity.

    If you’re looking to take a break from cycling, Poit’s Lighthouse Mini Golf offers an entertaining 18-hole miniature golf experience complete with lighthouse themes and a meandering river. Additionally, the iconic Nauset Lighthouse is available for tours, allowing visitors to appreciate a piece of restored maritime history.

    Restaurants

    While Orleans may not have as many attractions immediately adjacent to the trail, it more than compensates with its culinary offerings. Nauset Fish & Lobster Pool is renowned for its fresh seafood selection, and Land Ho! is a beloved local gathering place that serves a wide array of dishes to energize trail-goers. Over in Eastham, Arnold’s Lobster & Clam Bar is a must-visit for a sumptuous seafood feast, artisanal ice cream, and a round of mini golf. Alternatively, Red Barn Pizza & More is the spot for those craving pizza, pasta, subs, or burgers.

    Cape Cod National Seashore - Cape Cod Rail Trail
    Wellfleet | photo via Cape Cod National Seashore

    Finishing Your Rail Trail Cape Cod Adventure in Wellfleet

    Your journey across Cape Cod culminates in Wellfleet, situated at the midpoint of the Cape’s eastern stretch — between the tip and the elbow. If you embark on your adventure from here, there are two convenient parking options — the Cape Cod National Seashore headquarters on Marconi Site Road and the Wellfleet Trailhead on Lecount Hollow Road.

    Bike Rentals

    In Wellfleet, you’re presented with a couple of choices for bicycle rentals along the Cape Cod Rail Trail. The Little Capistrano Bike Shop and Idle Times Bike Shop maintain outposts in this town, ready to cater to your cycle repair and rental needs.

    Nearby Attractions

    Wellfleet’s standout feature is the Cape Cod National Seashore, encompassing 40 miles of diverse landscapes — including ponds, marshes, uplands, and pristine beaches. The park invites exploration with its wild cranberry bogs, an array of walking and biking trails, and historic lighthouses dotting the scenic coastline.

    Restaurants

    Near the Rail Trail, The Block & Tackle is highly recommended for its selection of smoked meats, sandwiches, fried chicken, and various snacks. For those with a taste for seafood, Van Rensselaer’s Restaurant & Raw Bar offers delightful options, while PB Boulangerie Bistro is the go-to for exquisite French cuisine.

    Old Colony Rail Trail - Cape Cod Rail Trail
    Old Colony Rail Trail | photo via Richard S

    Where to Pick Up the Cape Cod Rail Trail From Chatham

    Should you find yourself in Chatham and wish to venture onto the Cape Cod Rail Trail, the Old Colony Rail Trail serves as your gateway. This asphalt-paved path is suitable for easy to intermediate cycling levels and stretches westward to Harwich where it meets the Cape Cod Rail Trail at the Harwich bicycle rotary. Conversely, if you’re already on the Cape Cod Rail Trail, you can take a detour to visit Chatham.

    Stay at the Candleberry Inn Cape Cod Bed and Breakfast near the Cape Cod Rail Trail

    Where to Stay Near the Cape Cod Rail Trail

    As you travel along the Cape Cod Rail Trail, you’ll find a variety of accommodations. But for a centrally located stay, consider the Candleberry Inn bed and breakfast in Brewster. Our charming inn is ideally situated halfway between Yarmouth and Wellfleet, and it’s less than 1 mile from the trail.

    Candleberry Inn offers nine elegantly appointed guest rooms, each with its own luxurious touches, and provides a bike rack for those who opt to cycle with their own bikes. Beyond the comforts of our inn, Brewster boasts over a dozen restaurants and a plethora of local activities. We are also happy to recommend other Cape attractions and activities to enjoy during your visit.

    Check our availability when you’re ready to make plans for your Cape Cod getaway.

    Get our free Cape Cod Vacation Guide, full of the best things to do in Cape Cod. The best activities, restaurants, museums, events, views, and much more!

    Click here to request the guide.

    Share this post

    Share on facebook
    Share on pinterest
    Share on email