The Post itself is located at 3005 Dixwell Avenue, having been built in 1949. The late 1970's saw major changes with the sale of the Post's ball-field and picnic grounds that enabled key expansions and modernization of the building: upgrading the bar area, bathrooms, and building out 2 distinct halls(upper/smaller & downstairs/larger for well-needed revenue from rentals. 2023 saw the parking lot being re-paved, and 2025 brought on several projects to rejuvenate the property, inclusive of flooring, interior and exterior painting, as well as tiling of the bathroom floors.
Historical Highlights & Identity
Namesake: The post is named in honor of Corporal Kevin John “Jack” Dempsey. Dempsey was a local Hamden resident and a member of the U.S. Marine Corps who was killed in action during the Vietnam War. .
Early Recognition: Post 88 has a history of honoring local heroism beyond its own ranks. In March 1965, the Post famously presented its Meritorious Award to four Hamden firefighters who performed a dangerous "below-grade" rescue of a trapped workman following a road collapse on Skiff Street.
Military Support: The post has been active in supporting active-duty troops. One notable long-term project involved a massive "Box of Stuff" effort where members stood outside the local Walmart to collect supplies for soldiers overseas, shipping thousands of pounds of donated goods and letters from schoolchildren.
Post Activities & Community Role
Athletics: Like many Legion posts, Hamden Post 88 is deeply involved in American Legion Baseball. Their teams (often referred to as "Post 88") have a competitive history in Connecticut's Zone 4, providing a platform for local high school players to compete at a high level during the summer.
Service & Charity: The Post operates as a 501(c)(19) veterans organization. Its mission centers on "Veterans Strengthening America" through community service, youth programs (such as Boys State/Girls State), and providing a social hub for veterans at their "Canteen" or lounge.
Veteran Advocacy: The Post maintains a Service Officer to help local veterans navigate the complexities of VA benefits and claims, continuing the Legion’s founding mandate of "mutual helpfulness."
Today, Post 88 remains one of the most visible veteran organizations in Hamden, frequently leading or participating in town ceremonies for Memorial Day and Veterans Day.