We look for great people...


Who enjoy helping others.

We are relentlessly focused on creating a welcoming environment. We cut-to-order many of our products and guests are encouraged to sample and try something new. We look for team members with a warm and approachable consultative personality who are comfortable giving a big hearty "hello" from across the room.


Who don't mind getting their hands dirty.

In our shop we all mop the floors, clean the bathroom, do the dishes, and serve guests.  Our titles define unique elements of our job, but we all share the same priority - customer service. We look for detail oriented team members with a self-starter approach to completing tasks. 


Who love food and love to learn.

We're foodies helping out other foodies. We know that you might not be an expert in wine, spirits, and gourmet food - but we are looking for people who are interested in learning and open to exploring. We look for team members who like to cook, explore different cuisine, and like to learn about the way our food and wine is made, served, and paired. 

Job Responsibilities & Schedule


Customer service

All colleagues assist our guests in the selection of wine, spirits, cheese, and gourmet food. To successfully deliver on this responsibility, you must have a willingness to ask questions and engage customers. Successful candidates are also comfortable performing mental math, including: addition, subtraction, division, and calculate percentages.  Comfort navigating an iPad and using common iPad navigation and applications is required. Staff are expected to demonstrate ability to use our store software, NCR, within the first 30 days of employment. 

Product management

All colleagues participate in pricing, stocking, and inventory management. To accomplish this, colleagues must be able to lift 25 lbs. These tasks may be completed from a seated or standing position.

Store maintenance

We have a detailed set of daily and weekly cleaning activities that must be done to maintain a clean and food-safe environment. To accomplish this, staff must be able to read and follow oral directions. 


Friday, Saturday, and Sunday are our busy days of the week.  We commonly need assistance during these days. All candidates must be available to work weekend shifts, including major holiday weekends such as Memorial Day, Labor Day, 4th of July, Thanksgiving, and Christmas Eve. 

Kickstart your application process

Applying is easy. Fill in the form below and we'll get in touch.

Get to know us before you apply.

We expect that all applicants in the area visit our store before applying for a position with us. We encourage you to stop in and chat with our team, check out our products, and get to know us. 

Chester River Wine & Cheese Co.

117 S. Cross St., Chestertown, MD 21620, us

(443) 282-0220





10:00 am – 06:00 pm


10:00 am – 06:00 pm


10:00 am – 06:00 pm


10:00 am – 06:00 pm


10:00 am – 06:00 pm


11:00 am – 06:15 pm