It’s beginning to look a lot like Christmas.
The holiday season was kicked off this week in Annapolis with the annual Grand Illumination tree-lighting ceremony. It was a not-too-cold November night on Sunday when the Annapolis Jaycees, later joined by Santa and Mrs. Clauses, handed out hot chocolate and candy canes while school groups sang carols and danced to classic Nutcracker ballads, all before the 15-second countdown to light up the big Market House Christmas tree.
It is officially Christmastime in Annapolis. Holiday lights twinkle by City Dock, holiday shoppers rush in and out of boutiques downtown in search of the perfect Annapolis-themed gifts for faraway relatives, and Santa sightings are not an uncommon occurrence in our local restaurants, coffee shops, and art galleries. The Grand Illumination always marks the start of the holiday season just after Thanksgiving, but if you weren’t able to be there this year, don’t fret — there’s still an abundance of seasonal activities that you and your family can take advantage of this December. Here are just a few of the most festive family-friendly events this season in Annapolis.
On a nice night, go out and see the Lights on the Bay
Driving through the Lights on the Bay at Sandy Point State Park, a holiday tradition that’s sponsored by the SPCA of Anne Arundel County, is akin to being outside of Santa’s Workshop on Christmas Eve, except you don’t have to go far to experience this winter wonderland. The light show is open daily from 5 – 10 p.m., so you don’t have to work it into your schedule; go whenever you please!
Lights on the Bay
SPCA of Anne Arundel County is proud to announce the 24th annual Lights on the Bay holiday light show, open to the public on Saturday, November 17, 2018 and run through January 1, 2019.
Experience winter on the bay aboard the Jolly Express
If you have 45 minutes, then you have time to embark on a Jolly Express Cruise. The Jolly Express, known as Miss Anne during all other times of year, is adorned with Christmas decorations, and hot cocoa is served to riders while Santa steers the ship. The cruise runs on Fridays, Saturdays and Sundays (except Christmas Day) at 6, 7 and 8 p.m. A portion of the proceeds benefit Historic Annapolis.
Jolly Express Cruise
‘Tis the Season…for the Jolly Express! Hop aboard Miss Anne, all decked out for the Holidays and see the sights along Spa Creek on the Jolly Express. Miss Anne will be adorned with reindeer spirit for a 45-minute cruise including hot cocoa, holiday music and holiday cheer.
Take a walking tour downtown on the Holiday Candlelight Stroll
For non-sea-farers, the Holiday Candlelight Stroll is a similarly festive tour that presents a nostalgic remembrance of Christmases past. The 1 1/2-hour walking tour, held on Fridays and Saturdays (except Dec. 8) at 7 p.m., includes an outdoor evening stroll, an interior tour of the Hammond-Harwood House, and a lesson on the origin of many holiday traditions.
Holiday Candlelight Stroll
1 and a half hour walking tour. $21/Adults, $12/Children 3-11, Free 2 & Under Welcome the holidays with an evening stroll and a pleasant remembrance of Christmas past. Glowing lanterns light your way as you stroll around Maryland’s historic State Capital, all trimmed in holiday greenery.
Satisfy your cravings at the annual Chocolate Binge Fest
It’s literally the sweetest place to be this season. The 4th annual Chocolate Binge Festival returns to West Street on Dec. 2 from 12 – 5 p.m. and features entertainment, holiday shopping, and lots of chocolate under the lighting of the West Street Holiday Light Canopy. The festival also includes a giant gingerbread moon bounce, a fire pit for roasting marshmallows, a visit from Santa, and over 35 chocolate vendors.
Annapolis Chocolate Binge Festival
The Annapolis Chocolate Binge Festival is now in it’s fourth year. This family friendly festival includes entertainment, live music, chocolate, holiday shopping and the lighting of the festive West Street Holiday Light Canopy.
Knockout your holiday gift-buying while shopping local
Why shop at a mall during the day when you can shop at the beautifully decorated and illuminated shops of downtown Annapolis until midnight at Midnight Madness? Shoppers can stroll down Main Street, West Street, Maryland Avenue, State Circle, and Dock Street from 6 p.m. until midnight on Dec. 20 and until 11 p.m. on Dec. 6 and 13 in support of the city’s local businesses. The ambiance includes the Holiday Light Canopy over West Street, Snowflake Alley with entertainment, shopping deals, and treats to eat, and the Christmas tree at Market Space.
Midnight Madness: A Festive Shopping Experience in Downtown Annapolis
Downtown Annapolis Partnership proudly presents Midnight Madness-a Historic Downtown Annapolis holiday tradition that encompasses the charm and character of our most beloved memories of Norman Rockwell and Charles Dickens. We will adorn the streets and participating storefronts with holiday decorations, trees, garland, snowflakes, bows and lights to create a Downtown Winter Wonderland.
Enjoy all the lights in London Town
Sip cider and roast marshmallows at Historic London Town and Gardens, a “lost” colonial sanctuary on the South River, decked out for the season in holiday lights on Fridays and Saturdays between December 7 and 22 from 6 – 9 p.m. There will be special performances each week and even a doggie s’more stations provided by Dogwood Acres Pet Retreat.
Illuminated London Town
Experience the magic of a winter evening at Illuminated London Town! Sip hot cider and roast s’mores beside roaring fires in the Historic Area. Explore the gardens illuminated with festive holiday lights. Discover colonial nighttime festivities and holidays at a candlelit William Brown House, decorated for the season.
And, of course, watch the decorated boats drift by at the Yacht Club Lights Parade
What might be the most well-known holiday tradition in Annapolis is also one of the brightest: It’s the annual Eastport Yacht Club Lights Parade. Every year on the 2nd Saturday of December, boats parade down the Annapolis Harbor equipped with all kinds of lights, ornaments, music, and fun.
Eastport Yacht Club Lights Parade
Welcome to the Lights Parade! Every year on the second Saturday in December, magic happens on the water of the Annapolis Harbor…boats suddenly appear out of the cold winter night illuminated with thousands of colored lights and crewed by jolly revelers.
Pro tip: Prepare your parking plan before you leave the house if you’re visiting Annapolis on one of its busier nights this season. Happy holidays!
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