In 2005 the Barry family embarked on their second restaurant venture in Wellfleet. After 24 years of successfully running Moby Dick's Restaurant, the Barrys seized the opportunity and embraced a new challenge presented by the availability of the iconic Aesop's Tables in the fall of 2004. Partners David and Patricia Barry and their sons, Scott and Todd Barry and his wife Mignon, recruited the youngest Barry, Tracey and her new South African husband, Phillip Hunt, who brought managerial skills from the New York film industry, culinary talents and a passion for wine. After 14 weeks of intense cleaning, rebuilding and repairs - Winslow's Tavern opened to the public on June 11, 2005.

Winslow's Tavern is named honoring family Pilgrim ancestors who visited Wellfleet in 1620.
The historic building was first constructed in 1805 as a sea captain's home and was once the home of former Massachusetts Governor Channing Cox, who hosted President Calvin Coolidge for a night back in the 1920's. It has been a restaurant for 40 years.