How We Do The Holidays In Annapolis: Welcome to our Holiday Guide
How We Do The Holidays In Annapolis
Boat parades, Midnight Madness, cozy dinners, small shops and sparkling lights on the water. Here is how The Jen Holden Group actually spends the season and where we send friends who ask what to do.
Plan your holiday weekendIn this guide
The holidays bring something extra special to Annapolis. Lights sparkle across the harbor, downtown glows with greenery and bows, and neighbors bundle up for tree lightings, boat parades, and late-night shopping. It is that cozy, small-town holiday feeling with a coastal twist.
Since we live and work right here, we pulled our team together and asked everyone to share their go-to holiday events, traditions, restaurants, and local spots. Whether you are visiting for the first time or looking for new ideas close to home, we hope this guide helps you experience Annapolis the way locals do.
Holiday Events We Never Miss
Boat Parades On The Harbor
Jen’s number one pick is the boat parade, and Jane and Megan fully agree. The Eastport Yacht Club Lights Parade sends a line of boats through Spa Creek and Annapolis Harbor glowing with lights for one of the most magical nights of the season.
Midnight Madness Downtown
Midnight Madness came up again and again when we asked about favorites. On select Thursdays in December, shops stay open late, streets fill with music and twinkle lights, and downtown turns into one big festive block party. You can learn more and check dates on the Downtown Annapolis Partnership website.
Lights On The Bay
Anne’s pick is Lights on the Bay , a drive-through light display at Sandy Point State Park that benefits the SPCA of Anne Arundel County. It is easy with kids, wonderfully festive, and right on the Chesapeake.
- The Military Bowl and its downtown festivities
- Visits to Homestead Gardens for holiday decor and lights
- The team’s Toy Drive for Belle Grove Elementary School
- Breakfast with Santa at Kentmorr
- Early season skiing at Whitetail or Wisp when you need a little mountain time
For even more events, the Visit Annapolis holiday calendar is a great place to check dates and plan a full weekend.
Our Favorite Holiday Traditions
The big events are fun, but it is the little rituals that make this time of year feel like home. Here are a few traditions from our team:
- Jen: Loading up the family and heading to Hemlock Farm to pick out a real Christmas tree. It has become a sweet yearly ritual.
- Anne: Creating a big poster board with a square for each person. Everyone writes what they are thankful for, then they read their lists out loud together.
- Kristina: Walking around downtown during Midnight Madness, soaking in the lights, music and energy.
- Jane: Kicking off the season at the downtown tree lighting and Grand Illumination.
- Megan: Hosting a Turkey Football Bowl with friends for a little fresh air and a lot of laughter.
Real Tree, Fake Tree, And Where We Get Them
We learned quickly that people feel strongly about their Christmas trees.
Team Real Tree
Jen and Anne are firmly team real tree. Jen’s family heads to Hemlock Farm for a charming choose and cut experience. Anne’s crew loves picking out a tree from longtime local favorites Earleigh Heights or Diehl’s.
Team Fake Tree (With Real Tree Hearts)
Jane will always think of herself as a real tree person, but swears by the convenience of her Balsam Hill tree. Kristina laughs that she wants to be team real for the pine scent, but the trusty box of branches still comes up from the basement each year. Megan loves both, but her family currently has a fake tree at home.
Holiday Markets And Pop Ups We Love
Annapolis makes it easy to shop small during the holidays. Here are a few markets and pop-ups our team never misses:
- Vintage Christmas Market at Wildberry Farms and the Heroes Pub Holiday Market, both on Jen’s list for festive local finds.
- HERE. a Pop Up Shop, a traveling boutique that features local makers and seasonal gifts in different spots around town.
- The Annapolis Holiday Market at St. John’s College, which Anne is especially excited to explore this year.
- Midnight Madness itself, which doubles as a street long holiday market with shops open late.
- A rotating lineup of pop-up shops and boutiques that show up around Annapolis each December.
Best Spots For Holiday Drinks And Dinner With Friends
When it is time to warm up, catch up, and linger over something delicious, these are the places we keep coming back to:
Cozy Drinks And Cocktails
- Jingle Bell Bar at Red Red Wine Bar for seasonal cocktails and over the top holiday decor.
- Parley Room for a 1920s-inspired cocktail bar vibe right off State Circle.
- Preserve on Main Street, where the menu is thoughtful, creative and perfect for a cozy night downtown.
- Sailor Oyster Bar for oysters, bubbles and a lively, nautical atmosphere.
Favorite Places For Dinner
- Red Red Wine Bar for stone-fired pizzas, local seafood, and, of course, wine.
- Blackwall Hitch with its warm atmosphere, live music, and a coastal-inspired menu.
- Acqua al 2 and The Pearl for celebratory dinners that feel special but still relaxed.
Local Shops For Unique, Special Gifts
We are big believers in shopping local whenever we can, and Annapolis makes that easy. These are some of our go-to spots when we are looking for gifts that feel thoughtful and one of a kind:
- The Cottage for clothing, jewelry, accessories, and gifts on Main Street.
- Kim Hovell for coastal-inspired art, candles, and home pieces.
- Lilac Bijoux for casual chic clothing, jewelry, and accessories.
- The Lucky Knot for preppy, nautical style that feels perfectly Annapolis.
- Spots like Whimsicality, Lou Lou, Nordstrom Rack and Fresh Foods for fun little extras and gift baskets.
What We Are Asking Santa For This Year
This question says more about our hearts than our wish lists.
- Jen: Lots of powder ski days in 2026.
- Anne: Both grandkids together for the first time.
- Kristina: A year filled with health, peace and healing for family and friends.
- Jane: Good health, travel and special time with the people she loves.
Get The 2025 Annapolis Holidays Guide
Want a handy version of this holiday guide that you can click through, save to your phone, or print at home? We turned our favorite events, restaurants, shops, and local traditions into a flipbook covering Annapolis and Anne Arundel County.
Open the Flipbook GuideIf You Are New To Annapolis For The Holidays
First of all, welcome. Annapolis is a pretty easy place to fall in love with this time of year. Here are a few things we would tell you if we were chatting over coffee:
- Put at least one boat parade and Midnight Madness on your calendar.
- Walk downtown at night, wander through Snowflake Alley, and let yourself duck into the little shops that catch your eye.
- Plan a drive-through of Lights on the Bay and other light displays for an easy family night.
- Dress in layers. Waterfront views are beautiful, but the wind can surprise you.
- Look out for family-friendly events like Breakfast with Santa, the Military Bowl festivities, and neighborhood parades throughout the county.
If you find yourself falling for the cobblestone streets, the waterfront views, and the way this town sparkles in December, you are not alone. When you start wondering what it would look like to live here full time, our team would love to help you explore homes and neighborhoods that fit the way you want to live.
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