Westbury offers several distinct points of interest to consider when planning your trip: the history of the Flagstar at Westbury Music Fair, historic sites in the Village, and today’s cultural offerings. If you’re considering Westbury as a place to stay, you can tailor your search to whether you’re especially interested in theater, local history, or events.
Theater history at the Flagstar at Westbury Music Fair
The Flagstar at Westbury Music Fair is located at 960 Brush Hollow Road, Westbury, NY 11590. Its history began in 1956, when it opened as the Westbury Music Fair to host Broadway-style shows. The name Westbury Music Fair reflects the venue’s original purpose.
In 1966, a fully enclosed, round theater replaced the tent. This change made it possible to offer entertainment year-round. The two dates mark distinct milestones: the opening represents the start of Broadway-style shows, while the conversion marks the transition from a tent venue to an enclosed theater. This history offers a distinctive perspective on Westbury during your stay—especially if you’re interested in the history of stages and venues.
Historic sites in the Village
The Village of Westbury Heritage Trail identifies local sites within the Village as historically significant. The places it lists include the Westbury Monthly Meeting of the Religious Society of Friends, dated 1671, and the Westbury African Methodist Episcopal Zion Church, dated 1834. Both entries draw attention to different religious institutions and their historical context in the Village.
Another point of interest is the site of the Vanderbilt Cup Race Grandstand, which the Heritage Trail dates to 1904. Taken together, the trail’s selection includes religious sites and a historic grandstand site. The dates help distinguish these entries chronologically without grouping them all as the same type of attraction.
Collections are also among the listed sites. The Westbury Military Collection at the Westbury Veterans of Foreign Wars (VFW) Building at 403 Maple Ave. is included on the Heritage Trail; in 2024, the trail entry was updated to include the collection. The Historical Society of the Westburys preserves historic documents, photographs, and objects in a cottage at 445 Jefferson Street. The cottage is located between the Westbury Memorial Public Library and the Children’s Library. The historic offerings thus include landmarks, a collection in the VFW building, and materials preserved in the cottage.
Cultural offerings and other interests
Westbury Arts in the Village offers exhibitions and live performances, as well as hands-on workshops and community events. Its range spans formats that display or present art, workshops, and events for the community. If you’d like to take current cultural offerings into account when planning your trip, you can consider these different formats as a focus alongside theater and local history.
Samanea New York is a shopping, entertainment, and dining destination in Westbury, at 1500 Old Country Road. This offers a commercial destination with these three functions alongside historical and cultural attractions. The tenant mix may change, so take the current lineup into account when making specific plans.
Plan your stay around your interests
The Westbury Music Fair, the Heritage Trail’s historic entries, Westbury Arts, and Samanea New York each offer a different focus. To help you decide, you can first consider whether the history of a venue, historic sites and collections, cultural programs, or shopping and dining matter most to you.
Discover more destinations: Freeport, Oyster Bay, Rockville Centre, East Norwich, Mineola, Woodbury, Hicksville, Plainview.
For the broader travel overview: Nassau.
