The event will occur in the middle of the 600 block of Caroline Street and you may enter at the entrance near Billiken’s.  At check-in, you will be given a 21 and older wristband which needs to be worn during the entire event. At this time, you will also have the choice of purchasing a bottle of wine for your table or extra drink tickets. There will be cocktails, wine, and local beer available at the bar as well as tea, coffee and water. We hope that you will mingle and enjoy beverages and appetizers while you make your way to your designated seat. You will dine through six courses; appetizer, salad, pasta, fish, meat and finish the meal with dessert.

A Downtown Affair on Caroline is expected to take 3 hours.

A Downtown Affair on Caroline is best suited for flexible and adventurous eaters. Each attendee will receive the same fare, except there is a vegetarian option, if needed. When you place your ticket order, please let us know that a vegetarian option is desired. While, some plates may be flexible, there is no guarantee and no substitutions for strict restrictions such as vegan diets, medical diets, or sever food allergies. We apologize for this inconvenience. However, if you have questions about dietary restrictions, please email us at and we can advise you.

A Downtown Affair on Caroline is an experience for those 21 and older. Please do not bring children under the age of 21 years old.

Yes, ticket prices include unlimited non-alcoholic beverages plus two alcoholic drink tickets.  There is also a cash bar with unique wines, local craft beer, and cocktails. For the safety of our guest, please consider arranging for a designated driver within your party or plan for a driving service (Ex. Uber, Taxi) to get you home safely.  

Ticket prices are $150.00 per person (plus a Convenience Fee for Credit Card Processing) which includes unlimited non-alcoholic beverages, two alcoholic drink tickets, a cocktail hour with appetizers and six courses of local fare.

We accept online payment through our website. All major credit cards are accepted. If you desire to pay by check, please reach out to Ann Glave at or 540-538-7445. Mail checks to 904 Princess Anne Street, Suite 303, Fredericksburg VA 22401 payable to Fredericksburg Main Street Inc. There is a limited amount of tickets available for this event. Public tickets will be available as of July 1st.

Due to health department regulations, no pets (dogs, cats, lizards, birds, etc.) are allowed at A Downtown Affair on Caroline. Contact if you would like to get involved in the live auction or swag bags!

A Downtown Affair will take place in early October, we suggest you dress accordingly. We encourage bringing a light jacket in-case it gets chilly. Jeans and casual attire is appropriate.

A Downtown Affair will proceed rain or shine. If weather is not appropriate to be outdoors, we will announce our indoor location and any event location information as soon as possible via one or many channels of communication including our Facebook Event Page, email, or phone call.

We ask our chefs and restaurants to use the freshest ingredients and to be creative in their menu to give our guests a great taste of local fare. We will announce the menu as soon our chefs have a defined menu.

Due to the nature of the event, no refunds will be given for cancelations. However, if you cannot attend the dinner, you are welcome to transfer your ticket to someone else. Please contact us with the new guest’s information prior to the event.

We are encouraging usage of the City’s parking garage on Wolfe Street. There will be free parking for sponsors in the City’s parking garage. You will also be able to park on the near side streets.

Of course! We will have designated seats for those who need a little additional help. Please let us know when you purchase your ticket if you need an ADA seating arrangement. Reach out to



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