Annapolis Chocolate Binge Festival 2025

The Inner West Street Association brings you the popular Annapolis Chocolate Binge Festival to downtown Annapolis for the holidays. Held on Sunday, December 7th from 11 to 4 pm on the first block of West Street we have the Annapolis Chocolate Binge Festival, featuring family-friendly entertainment, chocolate, holiday shopping, and the festive West Street Holiday Light Canopy.

Start off the December holiday season with some fun and indulge your sweet tooth at the annual Annapolis Chocolate Binge Festival.

Take a chocolate tour along West Street with chocolate vendors selling various chocolate specialties, including chocolate truffles, caramels, bars, fudge, cookies, cakes, martinis, French macaroons, cupcakes, pies, brownies, and more.

Stop by Visit Annapolis at 26 West Street and vote for your favorite house at The Great Annapolis Gingerbread House. Winners will be announced at 3:30pm on Sunday, December 7th.

The Eastport Volunteer Fire Company will be collecting donations of non-perishable items to benefit local communities.

You can also complete your holiday shopping at our holiday market at the Annapolis Chocolate Binge Festival featuring local artisans with a wide range of handmade items including jewelry, pottery, candles, wood turnings, ornaments, and more.

The live music and entertainment start off at 11am and ends at 4 pm as the West Street Holiday Light Canopy lights up.

General Admission $5 plus Eventbrite fees.

Children Under 12 are FREE - No ticket needed

Sample taste tickets are 15 for $20 plus Eventbrite fees.

Stan & Joe's / Gray Wolf Spirits VIP Lounge

Chocolate Gingerbread House Decorating Contest

Have fun with Willy Wonka and Oompa Loompa's

Live Entertainment

Santa arrives at noon with Elfie

and More.....

Come out of the cold and relax for a bit! Stan and Joe's and Gray Wolf Spirits will be offering a pairing of their delicious menu paired with Gray Wolf and their all natural, and creative small batch spirits. Walk away with a Swag Bag with goodies from some of our Chocolate Vendors! Only 30 people per time slots will be gathered in the lounge. So grab your friends and reserve your time.

VIP Lounge Includes: One Ticket to the Chocolate Binge Festival, 15 Sample Taste Tickets, Stan and Joe's / Gray Wolf Spirits Tastings and a VIP Swag Bag with goodies.

Sign up for Lounge Event Times:

12:30 to 2:30 - Ticket Available

3pm to 5pm - Tickets Available

1. All Gingerbread houses must be delivered to the Annapolis Visitor Center at 26 West Street between 12:30 and 4:30pm on Saturday, November 22nd.

2. The public may vote during Visitor Center Hours on Sunday, November 24th through Sunday, December 7th.

3. All voting must be received by 3:30pm on Sunday, December 7th. The winner will be announced at that time.

All finalists will be on display through Friday, December 19th. All houses must be picked up by 4:00pm Saturday, December 20th.

Cash Prizes:

1st Place: $200

2nd Place: $100

Visit Annapolis Fan Favorite: $50

Kids 12 and under: $50 First Place

Kids 12 and under: $25 Second Place

Gingerbread House Contest Rules:

Any structure (house, church, school, barn, lighthouse, train, airplane or any other imaginative dwelling) may be entered.

The main structure can be constructed of either gingerbread or graham cracker. Original creations are encouraged, but purchased kits are certainly acceptable!

All components of the display, except the base, must be made of edible materials such as candy, nuts, cereal, cookies, crackers, pretzels, pasta, etc. All wrappers and lollipop sticks should be removed.

Houses may not contain any food item that needs refrigeration.

All structures must be mounted on a hard, unbending base.

Each contestant must fill out an entry from for his / her house.

Size limit for base is 24” x 24”. Entries need to be sturdy and should be able to be moved without consequence.

Do not write your name anywhere on your entry. The staff will assign your gingerbread creation a number.

Use the Royal Icing Recipe or at least a similar one. We cannot accept structures made with egg or butter icings as they can quickly turn rancid and also compromise the durability of the house.

Entries will be judged on the following criteria: originality, creativity, attractiveness and decorative appeal, workmanship, stability and durability.

Host or Publisher Inner West Street Association