It's that time again where the winds start to feel more like Jack Frost is nipping at your nose, twinkling lights and festive evergreen garlands dress storefronts and we begin to come together to celebrate the holiday season. If you happen to need a little help getting into the festive mood, you'll be happy to hear that our neck of the neighborhood in Annapolis has all manner of events to bring tons of cheer--as well as help you find that perfect gift for a special someone! Let's take a look at some of the winter wonderland events you can find!
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The Grand Illumination - Sunday After Thanksgiving
Kicking everything off the Sunday directly after Thanksgiving is the Grand Illumination of Downtown Annapolis' Christmas tree, with leadup events starting at 3:00pm in the Market Square area in front of Zachary's Jewelers (and right across from us! We promise to wave, and will be enjoying it with you!) From live music performances to ballet and cookies, cocoa and nutcrackers, it's a grand time leading up to Santa and friends appearing to light the tree around 5:15pm and spread some holiday cheer!
Annapolis Chocolate Binge Festival - First Sunday of December
The Sunday following the Grand Illumination is the Annapolis Chocolate Binge Festival up on the first block of West Street in the Arts District where they also host the First Sunday Arts Festival every first Sunday of the month May through November. Tickets are available online for only $5 with limited quantities available live at the event and free for children 12 & under, so be sure to come armed with your sweet tooth because it will be a decadent display of all manners of chocolatey confections, as well as a Gingerbread House Decorating Contest where winners will be displayed at the Visitor Center at 26 West Street. Running from 11:00am to 4:00pm ending with the illumination of the West Street Holiday canopy of lights, the Chocolate Binge Festival also runs alongside a holiday market with live music where you can get started on some holiday shopping with unique goods from local artists and makers as well.
Midnight Madness & 11th Hour - Every Thursday of December Until Christmas
What's a holiday season without a little madness? Every Thursday of December leading up to Christmas, shops downtown go all out helping you find special and unique gifts for friends and loved ones, including us! The first two Thursdays shops stay open until midnight, whereas on the third we're here until 11! Besides shopping, there's also live and festive entertainment with carolers, musicians and more--even alpacas outside the Alpaca International store. Take whimsical selfies in Snowflake Alley, enjoy some complimentary refreshments and snacks from some of the shops, and take in the ambience of our beautiful downtown area spanning from West Street to Main Street, to Maryland Avenue.
Oh! And come say hi! We'd love to help you find some special surprises for loved ones or even get you bundled up in a new swanky hat or knit to enjoy while you partake in the festivities!
Parade of Lights - Second Saturday of December
Of course, holiday entertainment downtown isn't just about wandering our historic streets, but also the whimsical fun to be seen on the water!
A tradition that started in the 1980s and hosted by the Eastport Yacht Club, members go all out to decorate their boats with all manner of light displays from the festively cute to silly and parade them along the water where onlookers can enjoy from pockets of parks with waterfront views in Eastport, to the bridge linking Eastport to downtown, and anywhere along the docks you can cozy up with some cocoa from 6:00pm to 8:00pm.
Santa Speedo Run - Second Saturday of December
If you're spending the day downtown earlier that Saturday before the Parade of Lights, you... may find a rather silly surprise: the Santa Speedo Run.
Based out of O'Briens Oyster Bar and Seafood Tavern, this annual even invites people to dress up in crazy costumes to run a trek through downtown around 12:30pm, while also being a donation drive accepting toys and food donations to give back to the community for those in need. It's a crazy event filled with good intentions, and the folks that participate get to enjoy libations, food and more at O'Briens to ward away the chill after and have a grand time!
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It's safe to say there are a lot of ways to get into the holiday season mood downtown, and we look forward to seeing you and yours to celebrate it all with us down at 103 Main Street!
