Only in Annapolis would you see a sailboat dressed as Frosty the Snowman. 

Our waterfront town goes all-out in the wintertime with glittering light displays, midnight shopping parties, and giant gingerbread houses. That dedication has even earned us international acclaim: Travel + Leisure ranks Annapolis as one of the best Christmas Towns in the USA. 

At Annapolis Waterfront Hotel, our central location is just moments away from the best holiday events in Annapolis. Explore this year’s top winter happenings with our insider guide, and plan your stay for an extraordinary holiday in Annapolis.

Midnight Madness

December 3, 10, and 17, 2026

Forget Black Friday – Midnight Madness is the ultimate holiday shopping moment in Annapolis. Each year in historic downtown, local Annapolis restaurants, boutiques, and art galleries stay open late on the first three Thursdays of December. While some are hunting for last-minute gifts, others ease into the night with extra-long dinners and bottles of wine. 

From Main Street to Maryland Avenue, the holiday magic is everywhere you look – carolers sing the classics, families snap photos in front of Snowflake Alley, and dazzling lights keep the spirits bright. Several participating shops and restaurants also offer discounts and complimentary drinks. Don’t miss the annual holiday tree at Market Space!

Chocolate Binge Festival

December 6, 2026 • 11:00 am – 4:00 pm

It doesn’t get more decadent than this. The annual Chocolate Binge Festival is a celebration of cacao in all its forms – truffles, cookies, lollipops, chocolate-covered fruit, elaborate French pastries, and anything else you can think of. 

This family-friendly tradition takes place every year on West Street in downtown Annapolis. Chocolate vendors line the block while nearby restaurants put their own spin on chocolate creations. 

The 2026 event will also feature a cooking demo with pastry chef Marisa Churchill, a boozy chocolate-and-spirits pairing, live entertainment, and artisan vendors with everything from jewelry to candles to handmade ornaments. 

44th Annual Eastport Yacht Club Lights Parade

December 12, 2026 • 6:00 – 8:00 pm

Ever seen a sailboat dressed as Santa Claus? At the annual Lights Parade, local creativity is on full display as dozens of sailboats transform into moving spectacles. Some yachts are simply decked in lights. Others take shape as grand holiday displays from giant Christmas trees, twinkling snowflakes, candy canes, and Rudolph, too. 

The event is free to attend for all ages. There are several vantage points along the waterfront, including Ego Alley and City Dock, both located directly outside of Annapolis Waterfront Hotel. 

Hoping for an up-close look? Experienced sailors can join a crew as a volunteer skipper. For those who’d rather kick back and relax, Watermark Journeys has a fun party cruise with festive music, cash bar, and a front-row seat to the action, all benefiting Annapolis charities.

Holiday Candlelight Stroll

Various dates, November – December 2026

Annapolis is one of the oldest cities in America, and it shows. Our red brick lanes, charming gas lamps, and 18th-century architecture feel even more nostalgic in the wintertime, a perfect moment for a holiday candlelight stroll. 

This guided tour is a seasonal tradition for residents and first-time visitors, led by local guides dressed in colonial costumes. Lanterns in hand, guests will wander through famous Annapolis landmarks – Victorian homes, hidden gardens, and historic shops – before they arrive at Market House Park, where a goody bag is waiting with George Washington’s famous eggnog recipe. 

28th Annual Annapolis Christmas Show

December 14 – December 15, 2026

There’s no party like the Annapolis Christmas Show, a holiday tradition for nearly 30 years. Taking place at Rams Head, an iconic concert venue in downtown Annapolis, the electrifying show is a two-day celebration of local artists and creative takes on famed holiday classics – think “Jingle Bell Rock” or Elvis’ moody “Blue Christmas”. 

Lights on the Bay 

November 23, 2026 – January 3, 2027

Along the shore of Chesapeake Bay, this drive-through holiday light show offers an easy, family-friendly experience. Winding through Sandy Point State Park, Lights on the Bay features nearly 70 animated and stationary light displays and a nightly scavenger hunt with exclusive prizes, plus surprise appearances from Santa and other holiday characters. 

A portion of proceeds benefit the SPCA of Anne Arundel County, a local animal shelter; naturally, family pets are welcome to join the fun.

Where to Stay: Annapolis Waterfront Hotel

Just steps from the harbor and downtown Annapolis, our boutique hotel is the perfect home base for celebrating the holidays and discovering everything the city has to offer.

With our Annapolis for the Holidays Offer, you receive 10% off your stay, two Holiday Spritz cocktails from Marmo upon arrival, late check-out (based on availability), and our Annapolis Holiday Guide, complete with a checklist of must-visit local festivities.