One of my favorite things about Osterville is its bike-friendly nature. The geography, roadways, and people encourage cycling. I try to bike almost every day and never tire of the ever-changing views and environments of the village.
The best place to begin your bike tour is in the center of the village, where there are ample places to park your car if you’re coming in from the outside.
Fuel up –but not too much – at the Chart Room
Head down to Parker Road to West Bay Road, which ends in the waters by Crosby Yacht. There are beautiful views here of the harbor and a fabulous array of boats. Even in the off season, when the boats are hauled and stored away, the view of the harbor is something else.
Even though it’s the beginning of our journey, it’s hard to resist the Chart Room. The restaurant has water views and a summertime ambiance as it is located adjacent to the harbor. Don’t eat too much before you continue the journey!
The view from the drawbridge
The next stop would be around the corner of Bridge Street. When you look to the north at the top of the Oyster Harbor drawbridge, you get a different perspective of the same harbor you viewed from the end of West Bay Road. Looking to the south, you can see the entirety of West Bay including the cut to Nantucket Sound. The slight elevation here lets you enjoy the full effect of the prevailing summer breezes from the southwest and the view of beautiful sailboats plying the waters.
Continuing the journey back down Bridge Street to West Bay Road, take a right to Eel River Road – follow this winding, rhododendron-lined byway to its end, which is Sea View Avenue. When you veer to the right, you hit another dead end and find yourself by the waters of West Bay. You’re now looking at the same body of water that you saw in the distance from the top of the drawbridge. You’re looking straight down Seapuit River, and you will see Cotuit in the distance as well as the southeast corner of Oyster Harbor’s island. What a beautiful vista.
The nicest sand on Nantucket Sound
Turn around and head east on Sea View Avenue to where it intersects with Wianno Avenue. That’s our next stop. Wianno Avenue ends right at the water, to a 60-foot-wide beach on Nantucket Sound.
My kids used to call this Straight Beach, because Wianno Avenue goes straight into the water. The beach is small here but has probably the nicest sand in the area. Looking to the southwest, you can see the vineyard on a clear day and feel the refreshing southwest summer breezes.
A food truck, a bathhouse, a fabulous place to spend the day
From “Straight Beach,” head up Wianno Avenue and take your first right on East Bay Road where you’ll find the entrance to Dowses Beach, which is exclusive to those who live there. Summer visitors can buy stickers that will allow them access to most of the beaches in town, but not to this one – you must be a resident. It is a beautiful beach with endless sand fronting the Nantucket Sound.
The southern exposure faces a smaller beach on East Bay, which is perfect for smaller people on windy days. You’ll typically find a food truck in the summertime with lifeguards, swimming lessons, and a bathhouse on the knoll overlooking the beach. It’s a fabulous place to spend the day in any season.
A secret garden in the heart of the village
From here, head back out to East Bay Road where you will soon find yourself at the intersection of Main Street. Across it is Armstrong-Kelley Park, the final stop of the tour. Surprisingly, this eight-acre horticultural wonder is a secret to many residents who don’t realize it exists in the heart of the village.
There are beautiful walkways and garden paths, carefully maintained by a dedicated group of village volunteers. It’s a great place to visit any time of year – bring lunch or dinner in a basket.
To end the tour, head back on Main Street to the village center, where you can stop at any of the fine restaurants or cafes to refuel. You can also pick up new accessories for your bike at the well-stocked Corner Cycle, as you contemplate and prepare for your next Osterville cycling adventure.
