Clio Logo
Better known today as the home of the popular Greenport Brewing Company, this sturdy building was once the Vail Brother’s car dealership. When the dealership started in 1920s it was the local Hupmobile franchise. The Hupmobile, an elegant well-built car grew in popularity until the Great Depression and overexpansion of the business ruined the company.

Vail Brothers Dealership c1950

Window, Font, Building, Facade

1925 Hubmobile Advertisement

Tire, Wheel, Motor vehicle, Car

Vail Brothers Motors Advertisements

Font, Poster, Parallel, Number

At the close of World War 1, Carl and Richard Vail decided to open a car dealership in a barn on the corner of the Main Road and Peconic Lane. After the brothers finished serving in the military, Carl who was a farmer, partnered with his brother Richard, who had experience working as a mechanic for the Sayre dealership in Southold.  

Originally a Hupmobile franchise, the business expanded over the next 55 years to include Buick, Pontiac and Packard. The brothers also did a side business in selling camping trailers made by the Covered Wagon Company. In 1974, Herb Wells took over the business, and it was renamed Wells Cadillac-Pontiac. The building went to become Michael Motors then Lucas Ford Trucks. Most recently the building has become the home and tasting room for the Greenport Brewing Company. 

Fleming, Geoffrey K. ed. In the Modern Era. Southold, New York: Town of Southold, New York, 2015.

Long Island Traveler-Mattituck Watchman. "The Largest Pontiac-Cadillac Dealer in the Smallest town in the U.S.A. ." July 11, 1974: 9.

Museum, Auto World. 1932 Hupmobile Roadster. 2020. (accessed April 7, 2021).

The County Review. "Hubmobile Eight." September 17, 1925: 36.

The County Review. "Vail Brothers Motor Co. ." August 20, 1936: 14.

Image Sources(Click to expand)

Town of Southold Historian's Files

The County Review - Town of Southold Historian's Files

The County Review - Town of Southold Historian's files