Cape Cod Horseback Riding Journey | Pretty Picky Properties
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Cape Cod Horseback Riding Journey

You came to Cape Cod for fun, a four-seasons climate, as well as the sand and water at the beach along the Atlantic Ocean. If you’re looking to fulfill a bucket list item Cape Cod horseback riding, you’ll find no shortage of places to go or companies to ride with. Most companies will want the age, height, and weight of riders in order to pair everyone with the appropriate horse. If you plan to ride on your own, a horse permit may be required.

Day 1:

Ridge Valley Riding Stables

Create a horse-riding tour of the Cape that suits your needs. Flexible schedules and the ability to start with helping load and transport the horses or meet the crew at the beach, your ride will no doubt be one-of-a-kind. The ride includes scenic views from the top of dunes, through scrub pine forest, near natural cranberry bogs, and onto the beach. Rides are for first-time riders all the way up to the most experienced equestrians. The 11-mile route starts at Sandy Neck Beach. Rides are available April, May, September, and October.

Meeting House Farm & Sanctuary

Take a guided trail ride with the company out of East Sandwich. They offer one-hour trail rides for beginners and 1.5-hour rides for intermediate and advanced-level riders, both age 14 and up. Special family rides are available for families with children under 14. Your knowledgeable guide will lead the way through Cape Cod conservation trails at a leisurely pace that suits everyone. Rides are by appointment only, and are available all year, even in the snowy winter!

Cape Cod Rail Trail

The trail is a paved trail that winds through Dennis, Harwich, Brewster, Orleans, Eastham, and Wellfleet, ending at the Cape Cod National Seashore. The whole of the trail is 22 miles, with intersections of Old Colony Rail Trail in Harwich and Nickerson State Park in Brewster. Enjoy scenic views and more but be sure to share the trail with hikers and bikers, too.

Day 2:

Haland Stable

Located in West Falmouth, the stable has serene and scenic surroundings perfect for a ride. If you’re in town for an extended period, the stable offers lessons for riders of all ages and skill levels. For the little ones, they also offer pony rides. The stable is open year-round.

CJ’s Ranch

Located in West Barnstable, the ranch offers lessons for riders of all ages and abilities. It’s the perfect place if you’re on a long-term vacation, and you can learn horsemanship in either Western or English disciplines. Lessons with Massachusetts licensed instructors will take you from getting aquatinted with the horse to your first horseback ride. If you’re in town with your child over their birthday, you can visit the ranch for a special pony ride!

Day 3:

Emerald Hollow Farm

The farm in Brewster is considered one of the best destinations for Cape Cod horseback riding lessons in all of Cape Cod. The family-owned business offers a range of lessons with a focus on “sustainable horsemanship.” The farm is great for long-term lessons, over the summer or any time of year. They’ll help you build a strong relationship with your horse. For those looking for a fun ride during a quick vacation, there are well-trained and suitable horses for all riders and all skill levels.

Highlander Horse Farm

Located in East Falmouth, the full-service equestrian facility. Choose from a casual horseback riding experience or a series of lessons. Experienced trainers work with riders of all ages and skill levels. Add in the scenic location with stunning ocean and landscape views and you’ll have the horseback riding experience of a lifetime!


There are a number cutting through the beautiful landscapes of Cape Cod. Visitors and locals can be found hiking and biking the trails. The horse lover in you wants to get out and explore the trails on horseback. Many of the same trails hikers and bikers frequent are prime for a horseback trail ride, too.

Cape Cod Horseback Riding Adventures

When you stay in a vacation rental in Cape Cod provided by Pretty Picky Properties, you’ll enjoy easy access to the beach and the crashing waves of the Atlantic. We’re also close to many area attractions, sites, tours, shopping, dining, and activities the area has to offer. Although our homes don’t have hitching posts for your equestrian friend, we are close to the many equestrian farms and companies offering trail rides in the area. Choose from a two-bedroom unit for a solo or sweetheart trip all the way up to a ten-bedroom compound for a Cape Cod horse-lovers getaway with all your loved ones.

Prepare a delicious home-cooked meal, in the fully equipped kitchen. Afterward, spread out in an open living space for a movie or to relax. Enjoy the view from the private balcony or patio or spend some time near the pool at select rentals.

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