About

In 2014 Pleasant Bay Community Boating purchased the 3.76-acre campus from the Edward F. McClennen family, who has owned the property since the early 1900s. Four dwellings and a boathouse are arrayed on the site, and their brief history follows:

Three Towns

The second oldest home on the bay, this dwelling was so named as the three towns of Orleans, Brewster and Harwich actually converge on this site. In 1889, Barley Field built a small summer cottage on this bare Pleasant Bay bluff, overlooking the Bay. The Edward F. McClennen family first rented the cottage (1903-1906), and purchased it in 1908, later calling it “Three Towns.” Over the years, the home was expanded upon to assume its current configuration. PBCB uses the building now for their offices.

Boathouse

Built in 1915, it was added on to in 1929 and again in 1947. The boathouse stored generations of McClennen family boats from Bay Birds to Mercurys, Whistlers, Beetle Cats, Day Sailers, Sunfish, Lasers, Windsurfers, Optimists, paddle boards and numerous row boats of varying sizes and shapes. The white “X” on a blue background on the boathouse doors represents the nautical flag “M” for McClennen which, coincidentally, matches the PBCB burgee! This is the base of sailing operations for PBCB’s current 80-boat fleet.

This is the base of sailing operations and houses PBCB’s current 80-boat fleet, which includes 12 Flying Scots, 8 Catboats, 4 Boston Whalers, 420s, Sunfish, and kayaks and sailboard equipment. The beach area to the left of the dock is reserved for PBCB visitors and spectators.

The Hillside Center and Topside

Located in Harwich at PBCB’s main entrance, this structure was built in 1928 as a three-car garage and a one-room playhouse upstairs. It was later converted to a year-round home in the 1980’s, with a guest room added on the upper slope. This dwelling currently houses our registration office. Renovated in 2018 in partnership with the Cape Cod Regional Technical High School and support from many local companies, the building is now utilized daily.  It is home to our summer Science & Sailing Camp students, and in the off season months it is used as meeting space by other partnering organizations, monthly Speaker Series events, and more.

South Cottage

Built in 1934 and located in the southernmost portion of the site in Harwich, this dwelling was expanded in the late ’30s and used as a summer cottage for the McClennen family. South Cottage is currently rented to individuals and families as part of our Residential Membership Program,  which provides much-needed revenue, while enabling visitors to “stay and sail” on our campus.

Square Top

Built in 1941 and named for the home’s shape, the house was modernized over the years, and is also available for rental during the summer months.