School is almost out and summer is right around the corner. All of us will soon be going out and enjoying ourselves before the impending fall and new school year. These last two featured businesses are well-known in the Brewster community and are perfect places to spend time with friends or family this summer.
Red Rooster
Red Rooster, a road-side attraction and restaurant found alongside Route 22, is considered a historical landmark in Brewster, especially in the eyes of those who live outside of the town. In fact, some people travel to Brewster specifically to visit the 1960s-themed restaurant. After opening in 1963, Red Rooster only continued to expand its brand and image, aiming to cater to the people of Brewster and those who pass through it. In 1967, former Carvel-manager Heinz Tiede took over management of the establishment, adding his own personal touch to the building. The iconic 6-foot ice cream cone that still stands on the roof today physically represents the legacy he brought to the Red Rooster name. Tiede is also responsible for the miniature golf course most families turn to once it warms up; it provides yet another fun activity that people can do this summer. Since 1993, Joseph Fiore has been the current owner of Red Rooster, taking his personal experience in the food industry and pouring it into this establishment.
What makes Red Rooster stand out in Brewster is not only its unique, vintage appearance and ambiance, but also its family-oriented atmosphere that the restaurant creates. The mini-golf course and carousel help develop this image of a family-friendly restaurant that is perfect to spend the afternoon with those closest to you. This paired with their famous soft-serve ice cream create the perfect experience, especially for hot summer days.
Something that Red Rooster prides itself on is the quality of their food. The restaurant aims to differentiate their food from “typical” fast food through its quality and readiness. Service is another attribute that the establishment wants to prioritize in order to maintain its honorable renown. The owner’s and staff’s goal is to provide a memorable service that makes customers feel appreciated, well-taken care of, and most of all, loved.

Wandering Dave’s
Located in the plaza right across from Red Rooster resides Wandering Dave’s. Many people remember Wandering Dave’s as a small food truck that used to work out of the parking lot of their now permanent home on Route 22. Known for their delicious farm-to-table food, the owner of Wandering Dave’s food truck, David Humpherey, was able to provide exemplary service to customers out of the 120 sq ft truck for over two years. Finally, Humpherey realized the only way to continue to grow business was to grow the space he worked out of, which prompted him to get a more stationary establishment in the shopping center in 2018.
Though they faced some obstacles when initially working in the new space, Humphrey and his team were able to create the brand we all know and love today. Day in and day out, Wandering Dave’s continues to serve fresh food with amazing quality while gathering loyal customers with their sustainable practices; the majority of their ingredients are locally sourced, typically from the Hudson Valley region. By having a larger space, Humphrey was able to experiment more with his cooking, allowing the restaurant to serve more than just fresh tacos and fries. The restaurant now serves a wide variety of food, ranging from salads to ramen dishes in addition to their famous tacos and delicious truffle fries, which are made fresh with every order.

Humphrey still makes it a priority to uphold his food quality and standards in both his food truck and his restaurant. The positives of having the two businesses is the increase in clientele that comes with it. When the food truck is booked for the event, people can turn to the restaurant as another option and vice versa. Wandering Dave’s has maintained its values that it had when it was just a food truck and if they continue to uphold them, then the business will only continue to prosper and expand like it has already.
These two businesses are staples in Brewster and even help attract people to the town. Though they both were established decades apart, both establishments uphold similar principles of good service and good quality of food, which has contributed to their successes. Whether you want a refreshing milkshake or tasty truffle fries, Red Rooster and Wandering Dave’s are definitely good spots to eat at this coming summer!