Annapolis Scavenger Hunt: App-Led Adventure Through Red Bricks

Navigate Annapolis on your own terms, solving clues and earning points as you go.

A self-guided scavenger hunt through Annapolis where you download the Let's Roam app, start whenever you choose, and work through trivia questions and photo challenges tied to real landmarks and hidden details around the city. You move at your own pace with your group, each person taking on an interactive role, and the app guides you through the entire experience without a tour guide or fixed schedule.

The experience

Annapolis's scavenger hunt works entirely through your smartphone. Download the Let's Roam app, redeem your ticket, and you're ready to begin: no guide, no meeting time, no waiting. The app feeds you trivia questions that can only be answered by finding specific plaques, statues, art and other details scattered through the city, so you're actually looking at what makes Annapolis worth seeing instead of just walking past it. Each person in your group gets their own interactive role and receives texted photo challenges tailored to them, turning the hunt into something between a game and a guided tour, except you're in control of the route and the rhythm.

The whole thing runs 1.5 to 2 hours depending on how much you linger at each stop and how competitive you get with the photo challenges. You earn points for the best shots, so there's a reason to actually engage with what you're seeing rather than just checking boxes. This works for groups of friends, family outings, birthday celebrations, bachelorette parties looking for something more active than a bar crawl, or corporate teams that need to actually work together instead of just standing in a room. The app keeps score and tracks progress, so if your group wants to compete or collaborate, the structure is already there.

Start whenever suits your day: morning, afternoon, whenever you and your group are ready. Make sure your phone is fully charged or bring a power bank, since you'll be using the app the whole time to navigate and interact with the challenges. Comfortable shoes matter. You'll be walking through the city hitting multiple stops. The hunt is wheelchair accessible, and children as young as five can join, though the physical demands mean you should be comfortable with a moderate amount of walking.

What’s included

• Let's Roam app access.
• self-guided navigation through Annapolis.
• trivia questions tied to real landmarks.
• personalized photo challenges for each player.
• point scoring and group leaderboard.

Before you book

Days and timesEvery day

AgesAdult (18 to 50 years) · Senior (51 to 65 years) · Youth (11 to 17 years) · Child (5 to 10 years) · Under 5: can't be booked

GroupPrivate

Meeting point and pickupNo hotel pickup: you go to the meeting point. Ends back at the starting point.

Cancellation and refundsFree cancellation up to 24 h before the start. After that, no refund.

Prices and times updated 2 days ago

Good to know

Moderate physical effortWheelchair accessibleStroller-friendlyPets welcomePublic transport nearbyNot recommended during pregnancyNot recommended with heart problemsNot recommended with back problems

Operated by Let's Roam

Is this one for you?The pace is entirely yours. You set how fast you move between stops and how long you spend at each one. If your group wants to linger at a landmark or move quickly to the next challenge, the app adapts to you rather than the other way around.

Traveler reviews

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Top questions

Can children come?

Yes. Ticket types: Youth (11 to 17 years); Child (5 to 10 years). Children under 5 can't be included in the booking.

Can I start the scavenger hunt whenever I want, or is there a set time?

You start whenever you choose. This is a self-guided hunt with no fixed departure time or reservation required, so you can begin in the morning, afternoon, or whenever your group is ready to go.

What do I need to bring to do the Annapolis scavenger hunt?

A fully charged smartphone to run the Let's Roam app. Bring a power bank if you're worried about battery. Comfortable walking shoes and weather-appropriate clothing are recommended since you'll be moving through the city for 1.5 to 2 hours.

How does the app guide me through the hunt if there's no tour guide?

The app displays trivia questions and photo challenges, then directs you to specific locations around Annapolis where you find the answers hidden on plaques, statues, and other landmarks. The app tracks your progress and keeps score as you complete each challenge.

Is this scavenger hunt good for groups, or can I do it solo?

It works for both. The hunt is designed for groups where each person gets an interactive role and receives their own photo challenges, but you can also do it alone if you prefer. Either way, the app guides you through the same experience.

What makes the photo challenges part of the hunt?

Each person receives texted photo challenges specific to their role, and you earn points for the best photos your group takes. It adds a creative layer to the hunt and gives everyone a reason to engage with the landmarks and each other.