Hit the Road, Osterville walks, waking and bike routes

There’s no better way to get to know Osterville than to hit the road on foot or bike. And, for those who like to wander off road, we’ve got some great options as well. These great routes will reward you with great views along the way.


All of the routes in this section start at the Osterville Village Library on corner of Wianno Avenue and West Bay Road (in front of the Osterville Library, looking at the post office across the street).

The Big Loop 5.5 miles

Go right and head down Wianno Avenue to the end, where you can pause for a great view of the ocean. Turn right onto Sea View Avenue. You’ll see the stately Wianno Club on your left. A successful summer hotel called The Cotocheset House was built in 1873 and stood on this site. The foundation of the hotel was made of stone taken from Daniel Webster’s Boston mansion which had been destroyed by fire in 1872. The Cotocheset House itself burned to the ground as well in 1887, but was immediately rebuilt. The “new” Cotocheset House, the present Wianno Clubhouse, opened in July of 1888. Continue to the end of Sea View Avenue and enjoy the views of Sampsons Island and Oyster Harbors across the water. To return, head back down Sea View and take a left onto Eel River Road. At the end, take a right on West Bay to get back to the village, or take a short detour to the left to visit Crosby Yacht Yard, where boat building and repair has taken place since the early 1800s.

Train for the Road Race 3.1 miles

All of the routes in this section start at the corner of Wianno Avenue and West Bay Road (in front of the Osterville Library, looking at the post office across the street).

Prepare for the Annual Cape Cod 5K Championship (Village Day, 8 AM). Start in front of the Osterville Village Library, straight to Wianno Ave, right onto Seaview Ave. As you turn right onto Parker Road, say good bye to the ocean views, but the beauty of the Wianno Golf Course awaits you. Mile 3 is at the intersection. Onto Parker Road and West Bay Road; take a right onto West Bay Road for the last 1/10 th of a mile and finish right back near where you started. To register visit the Osterville Village Library

Oyster Harbors Windmnill and Back   Distance: 3.1 miles

Take a right onto West Bay Road and stay straight when you reach Parker Road. The Osterville Historical Society Museum will be on your left. The Museum’s lovely grounds include an 18th century herbal garden and a 19th century ornamental garden, and are also home to Osterville’ s Farmers Market in the summer months. Take a left onto Bridge Street. Stop and enjoy the views on both sides of the bridge (beware that it’s a draw bridge); continue until you reach the windmill, the entry to Oyster Harbors, a private residential enclave. Retrace your route to return to the village. 

Easy Bay Route    2.7 miles

Go right onto Wianno Avenue. Take a left onto East Bay Road. You’ll see Dowses Beach on your right. Take a detour in to either walk the beach or bike through the parking lot to the end. Stop to enjoy the view from the observation deck and check out who is catching what on the jetty. Go back out to East Bay Road and take a right. At the end of East Bay Road take a left. Armstrong-Kelley Park is on your right.  To finish your walk, continue on Main street and then take a left on West Bay Road.

Go Off Road

Two great woodland areas to escape the beach crowds. One warning for anyone heading off road to hike: stay on trails to avoid ticks and poison ivy. It’s best to wear long pants tucked into socks, and check yourself for ticks after your hike.

Skunknett River Wildlife Sanctuary

Located just off Bumps River Road, this sanctuary has more than 100 acres of woodlands. Walk along the sanctuary’s tree-covered trails to a small woodland pond where you may see great blue herons, black-crowned night-herons, and ospreys. In the spring, listen for chorusing frogs in the vernal pools. For directions and more information: 508.362.7475/508.362.7475 or longpasture@massaudubon.org.

Joshua’s Pond

Located just off Tower Hill Road. As you drive into the parking lot, the trail 

is to the right of the pond. Be careful not to turn an ankle on protruding tree roots along the way. The path winds along the shore of Joshua’s Pond. About ¾ of a mile into the loop there is a fork. Keep to the left, continue to follow the path and about another ½ mile along you’ll find yourself with Joshua’s Pond on one side and Micah’s Pond on the other. Don’t be surprised to see red tail hawks, or even a stray deer. The path continues to wind around Micah’s Pond and brings you back onto Pond Street. Or, retrace your steps to the Tower Hill Parking lot.

- Claudia Mahoney

Armstrong-Kelly Park is a beautiful oasis for strolling the boardwalk, hiking the short trails, or just sitting and enjoying the view.


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