Parking in downtown Annapolis can be a hassle but as a local DC are a mom I am sharing all my tips to keep it as stress free as possible! Annapolis is one of our favorite day trips—charming streets, walkable waterfront, and plenty of low-key adventures for little ones. In this post, I’m sharing everything: where to park near the most kid-friendly attractions, how to ride the free trolley, and tips for navigating busy event days like a pro!
Parking Downtown Annapolis Maryland - Table of Contents
- Best Parking Garages
- Free & Discounted Parking
- Street Parking & App Tips
- Free Trolley
- Event Days & High-Traffic Tips
- Top Kid-Friendly Things to Do in Annapolis (and Where to Park!)
Top Parking Annapolis Downtown Garages for Families
Hillman Garage (150 Gorman St.)
Recently renovated, Hillman Garage offers smart technology, EV charging stations, and is centrally located near Main Street and City Dock. It's stroller-friendly and ideal for families visiting downtown attractions.
Gotts Court Garage Annapolis Downtown Parking (25 Calvert St.)
Adjacent to the Visitors Center, Gotts Court Garage is perfect for first-time visitors. It features a gateless entry system, making parking hassle-free.
Knighton Garage (1A Colonial Ave.)
Located near West Street, Knighton Garage offers discounted rates after 4 PM, making it a budget-friendly option for evening outings.
Park Place Garage (1 Park Place)
Situated at Westgate Circle, Park Place Garage provides ample parking and is connected to downtown via the free Circulator Trolley.
Free & Discounted Parking Tips for Downtown Annapolis
- Sundays: Enjoy free parking at Whitmore Garage(25 Clay St.) when entering after 6 AM and exiting before 4 PM.
- Evenings: Bladen Street Garage offers free parking from 6 PM to 6 AM on weekdays and all day on weekends.
- Calvert Street Garage: Provides free weekend parking and is a short walk to historic sites.
- Use the Free Trolley see below!
Street Parking & App Tips for Downtown Annapolis Maryland
- Metered Parking: Rates start at $3.25 per hour on commercial streets and $4 per hour on residential streets. Most meters have a 2-hour limit. downtownannapolispartnership.org
- Payment: Use the ParkMobile app to pay for parking and extend time remotely.
- Free Holiday Parking: During the holiday season, enjoy three hours of free parking at metered spaces.
Annapolis Circulator Trolley
Use the Annapolis Circulator Trolley for free transportation from outer garages into the heart of downtown!
The Downtown Trolley runs on Saturdays and Sundays from 11 am to 5:30 pm. The Annapolis Circulator Trolley is a free and family-friendly shuttle that loops through downtown, connecting key parking garages to popular spots like Main Street and City Dock. It’s stroller-accessible and runs every 10–15 minutes, making it a convenient way to avoid long walks with kids in tow.
If you’re parked a bit outside the downtown core, the free Circulator Trolley is a lifesaver. It’s an easy, no-cost way to get around historic Annapolis, especially for families carrying snacks, gear, or tired toddlers. Just hop on at one of the marked stops near public garages like Park Place or Knighton.
Mom Tip: I would definitely recommend you check out the map ahead of time. Such a cool way to add fun to your day trip to Annapolis!
Annapolis Event Days & High-Traffic Tips for Parking Downtown
Downtown Annapolis hosts several major events each year that draw large crowds and can make parking a challenge—especially for families. To ensure a smooth visit, it's essential to plan ahead. Arriving early, utilizing park-and-ride options, or considering alternative transportation like the Circulator Trolley can help avoid congestion. Below are some key events for 2025.
Annapolis Boat Shows
- 2025:
- Spring Sailboat Show: April 25–27
- Powerboat Show: October 2–5
- Sailboat Show: October 9–12
These events transform the City Dock area into a bustling hub, attracting boating enthusiasts from all over. Parking garages fill up quickly, so consider using the free Circulator Trolley from Park Place Garage or other park-and-ride options.
U.S. Naval Academy Commissioning Week
- 2025:
- Graduation Ceremony: May 23
- Blue Angels Flight Demonstration: May 21, 2025
Commissioning Week is a significant event, culminating in the graduation of midshipmen. The Blue Angels' flight demonstration is a highlight, drawing large crowds. Expect road closures and increased traffic. Arriving early and considering alternative transportation methods is advisable.
Fourth of July Celebrations
- 2025 Parade and Fireworks: July 4
Annapolis's Independence Day celebrations include a parade through downtown and a fireworks display over the harbor.These events attract large crowds, and parking can be scarce. Utilizing park-and-ride options or arriving early can help ensure a more enjoyable experience.
Top Kid-Friendly Things to Do in Annapolis (and Where to Park!)
Whether you're visiting for a day or a weekend, Annapolis offers plenty of activities that are fun for kids and easy for parents. Here’s a list of popular family-friendly attractions—and exactly where to park to make your visit smooth. And I also have another list of 16 Things to Do with Kids in Annapolis here to check out some hidden gems!
1. U.S. Naval Academy Visitor Center & Museum in Annapolis
Why Kids Love It:
- Walk through naval history, view model ships, and check out real midshipmen in uniform.
- Free admission with ID for adults.
Best Parking Annapolis Downtown:
- Gotts Court Garage (5-minute walk)
- Hillman Garage (closest overall once reopened)
Insider Tip: Bring a stroller or baby carrier for toddlers; the Academy grounds are spacious.
2. City Dock & Ego Alley Downtown Annapolis Parking
Why Kids Love It:
- Watch boats come in and out of the harbor.
- Feed ducks, grab ice cream, or hop on a boat tour like the Harbor Queen.
Best Parking Annapolis Downtown:
- Hillman Garage (steps away from the dock)
- Park Place Garage + free Circulator Trolley
Nearby Treats: Storm Bros. Ice Cream and Kilwins Fudge Shop.
3. Annapolis Library at West Street
Why Kids Love It:
- Story times, interactive play zones, and a modern, airy kids’ area.
Best Parking:
- Knighton Garage (short walk across West Street)
- Gotts Court Garage (a little farther, but near restaurants)
4. Pirate Adventures on the Chesapeake
Why Kids Love It:
- Dress up like pirates, follow a treasure map, and cruise on the bay in a themed ship.
- For ages 3–10 (advance tickets highly recommended).
Best Parking:
- Eastport Lot (at 306 2nd St.)
- Hillman Garage + short walk over the Spa Creek Bridge
5. Acton’s Cove Waterfront Park
Why Kids Love It:
- Small playground and peaceful waterfront paths.
- Great for picnics and letting little ones stretch their legs.
Best Parking Annapolis Downtown:
- Gotts Court Garage or Hillman Garage, both within 10 minutes’ walk
6. Browse Shops on Main Street
Why Kids Love It:
- Toy stores, bookstores, and snack spots make Main Street a kid-friendly stroll.
- Plenty of window displays and street performers during warmer months.
Best Parking:
- Hillman Garage (right at the bottom of Main Street)
- Gotts Court Garage
With these tips, I hope your family can enjoy all that downtown Annapolis has to offer without the stress of parking!
