Look, everyone thinks Annapolis basically shuts down once the sailboats are hauled out and the "Boat Show" madness of October fades into memory. They’re wrong. Honestly, if you’re heading downtown expecting a ghost town, you’re in for a shock. The "Dark Ages"—that stretch between New Year's and St. Paddy's Day—is actually when the locals finally get their city back, and it's probably the best time to visit if you actually want to hear yourself think.
This weekend, January 17th and 18th, 2026, the city is leaning hard into that cozy, brick-lined vibe. You've got live jazz, a surprising amount of college wrestling, and the kind of historical deep dives that are usually too crowded to enjoy in July. Whether you’re a local looking to kill a Saturday or a visitor brave enough to handle the Chesapeake breeze, here is the real deal on things to do in Annapolis this weekend.
Live Music and the West Street Scene
If you haven’t been to Rams Head On Stage lately, you’re missing the heartbeat of the Annapolis evening. This place is tiny. It’s intimate. You’re basically sitting in the performer's lap, which makes for an incredible show but a weird place to eat a burger.
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On Saturday, January 17, Jarrod Lawson is taking the stage. If you don't know him, think soul-jazz fusion with a heavy dose of Stevie Wonder vibes. It’s the perfect antidote to a gray January afternoon. Then, on Sunday, January 18, Avery*Sunshine brings her mix of gospel and R&B to West Street.
Pro tip: West Street is the "Arts District," but it's also where the best dinner-and-a-show logistics happen. You can grab a drink at 49 West Coffeehouse across the street before the show. They usually have a rotating art gallery on the walls that’s worth a look while you wait for your latte or Pinot.
Saturday Night Vibes
- Jarrod Lawson at Rams Head: Doors usually open early for dinner.
- Pherm Brewing Company: If you don't mind a 15-minute drive out to Gambrills, Kevin Driscoll is playing on Sunday. It’s a bit of a haul, but the beer is legit.
The Military Side of Things: Navy Sports
Most people walk the perimeter of the U.S. Naval Academy and call it a day. That's a mistake. The yard is open to the public (bring your ID!), and this weekend is surprisingly heavy on the sports schedule.
On Sunday, January 18, the Navy Midshipmen are hosting George Mason for a wrestling meet at Alumni Hall. There is something intensely "Annapolis" about watching a wrestling match on a military campus in the middle of winter. It’s high energy, it’s loud, and it’s usually pretty cheap to get in.
If you're more into hoops, the Navy Women's Basketball team is taking on Lehigh on Saturday. It’s a great family-friendly option because, let’s be real, trying to drag kids through a 18th-century museum for four hours is a recipe for a meltdown.
Getting Your History Fix Without the Crowds
Things to do in Annapolis this weekend for History Nerds
The Maryland State House is the only state capitol that served as the nation's capitol for a hot minute (1783-1784). It’s also where George Washington resigned his commission. This weekend, you can actually walk into the Old Senate Chamber and stand exactly where he stood without being elbowed by a tour group of forty people.
Watermark is running their "Colonial Annapolis & Maryland State House" tours both Saturday and Sunday at 1:30 PM. A guide in a tri-corner hat walks you through the historic district and into the State House. It sounds touristy. It is touristy. But honestly? The stories about the "Golden Age" of Annapolis are actually fascinating once you get past the costume.
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Historical Highlights to Hit:
- The Maryland State House: Open 8:30 a.m. to 5:00 p.m. Remember your physical ID. No photos on your phone.
- William Paca House: The gardens are dormant right now, but the house tour is a great way to see how the 1% lived in the 1770s.
- Kunta Kinte-Alex Haley Memorial: Located right at City Dock. It’s a quiet, reflective spot that most people breeze past on their way to buy a t-shirt. Don't be that person.
The Winter Dining Strategy
Eating in Annapolis during the summer is a battle of wills. This weekend? You can actually get a table at Chick and Ruth’s Delly. Yes, they still do the Pledge of Allegiance. Yes, the milkshakes are still massive.
If you want something a bit more upscale, Annapolis Restaurant Week prep is usually in full swing this time of year. Many places like Cooper’s Hawk or The Melting Pot offer weekend brunch specials or "Thursdate" deals that carry over.
But if you want the "real" local experience, head over the bridge to Eastport. Go to Davis’ Pub. It’s small, it’s divey, and the crab pretzel is the stuff of legend. It’s the kind of place where you’ll see sailors in yellow foul-weather gear even if there isn't a cloud in the sky.
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Rainy or Cold Weather Backups
If the Chesapeake wind starts biting too hard, the Busch Annapolis Library is weirdly active this weekend. They’re running a "Shakespeare in Cinema" series on Saturday at 2:00 PM, showing Shakespeare in Love.
They also have a Dungeons & Dragons group meeting at the same time. I’m serious. If you’ve ever wanted to watch a level 5 party take on a beholder while it’s 40 degrees outside, that’s your spot.
Family Friendly Checklist:
- Preschool LEGO Build: Saturday morning at the library.
- Family Storytime: 10:30 AM at the Eastport-Annapolis Neck branch.
- Ice Skating: Check the local schedule at Quiet Waters Park. The rink there is outdoors but well-maintained, and the surrounding trails are great for a winter hike if you've got the boots for it.
Actionable Next Steps for Your Visit
Don't just wing it. Annapolis is small, but the parking is a nightmare even in January.
- Park once: Use the Hillman Garage right off Main Street. It was rebuilt recently and is much easier than circling the block for street parking.
- Check the ID: You need a physical government ID (no digital copies) to enter the Naval Academy or the State House. If you forget it, you’re stuck looking at the gates.
- Dress in layers: The wind off the Severn River is no joke. It can feel ten degrees colder at City Dock than it does just three blocks up on Maryland Avenue.
Book your tour tickets for the State House through Watermark’s website ahead of time to ensure a spot, and if you’re planning on dinner at Rams Head, grab those tickets now—Jarrod Lawson is a big draw for the jazz crowd. Enjoy the quiet side of the city. It won't stay this way once the weather warms up.