Triangle Diner™ (Founded 1948)

Listed on the National Register of Historic Places and the Virginia Landmarks Register

Serving History and Food for Over 75 years!


Triangle Diner Triangle Diner Parade

Classic 1950s Diner Architecture

Triangle Diner™, located at 27 W. Gerrard St., Winchester, VA, is a historic restaurant and catering establishment. Built in 1948 by the Jerry O'Mahony Diner Company, it remains one of America's best-preserved classic 1950s diners.

The diner features a stainless steel exterior, rounded corner windows, and a distinctive barrel-vaulted ceiling with hidden reflective lighting. Inside, customers enjoy seating for 50, including floor-mounted stools at a vintage counter, reminiscent of the golden era of American diners.

Triangle Diner is one of the few remaining examples of stainless-steel diners manufactured by the O'Mahony Company, which were shipped across the country in sections and assembled on-site.

Patsy Cline’s Connection to Triangle Diner

Country music legend Patsy Cline, a Winchester native, worked here after dropping out of Handley High School (across the street) in 1948 to help support her family. She was just a teenager at the time, working as a waitress while pursuing her passion for singing.

National and State Historic Recognition

Due to its architectural significance, Triangle Diner was listed on the National Register of Historic Places by the U.S. Department of the Interior on March 31, 2010. It was also added to the Virginia Landmarks Register on December 17, 2009, recognizing its contribution to American cultural heritage.

Off-Site Catering Services (Contact Us)

Though our dining room is temporarily closed for historic renovation, our catering and food truck services are fully operational. Triangle Diner offers exceptional catering and food truck services. Give your guests a themed 1950s food experience at your corporate event, festival, or private celebration. Our professional chef-driven catering ensures an unforgettable culinary experience. We now provide catering services to all areas in Virginia, Washington, DC, and Maryland in 2025. We specialize in large events, such as festivals and community events. We serve thousands of funnel cakes at the Shenandoah Apple Blossom Festival.

Our Private Catering Services Include:

  • ✅ Customized Menus
  • ✅ On-Site Hot Cooking
  • ✅ Staffed or Drop-Off Service

Perfect for Any Occasion:

  • ✅ Corporate Events
  • ✅ Community Festivals
  • ✅ Private Parties

Our Specialties:

  • ✅ Gourmet Burgers
  • ✅ Funnel Cakes
  • ✅ Milkshakes
  • ✅ DIY Ice Cream Sundae Bar
Funnel Cake

Funnel Cakes

Our signature crispy, golden funnel cakes are topped with powdered sugar, chocolate drizzle, or fresh fruit.

Ice Cream Bar

Ice Cream Buffet

Customize your ice cream with a variety of flavors, sauces, fresh fruit, and homemade whipped cream.

Gourmet Burger

Gourmet Burgers

Enjoy handcrafted burgers made from premium beef, fresh brioche buns, and delicious toppings.