Feel your pulse quicken as you explore Annapolis Scavenger Hunt, Downtown quests, Naval Academy challenges, St. John's College routes, spirited Bar Crawls, or spine-tingling Ghost Tours—all against the backdrop of historic plazas and vibrant murals.
Gather your friends or family for trivia quests, bold photo dares, and wild challenges—earn points through our app as you compete for bragging rights and share laughs along every route!
Top Outdoor Activities In Annapolis, Maryland
Colorful sailboats dance across the Chesapeake Bay as you step into Annapolis, Maryland's Capital City. Whether you are a first-time visitor or a local, these outdoor activities invite you to uncover the city's vibrant heart and hidden corners. Experience the lively buzz of Historic Downtown Annapolis while discovering must-see sights through engaging adventures. Outdoor activities here offer an energetic, unforgettable way to view Annapolis from new perspectives.
Adventurers exploring in Annapolis!
Outdoor Experiences in Annapolis, Maryland
Get ready for an adventure-packed journey with our expertly curated list of outdoor activities in Annapolis! Each experience is designed to showcase unique city highlights, from iconic waterfronts and art-lined streets to historic campuses and legendary nightlife spots. Discover something new at every turn—whether it is a thrilling bar crawl, a mysterious ghost tour, or a challenge-filled quest through famous landmarks. Dive into these top-rated activities and see why exploring outdoors is one of the best things to do in Annapolis.
Top Rated
5.0 (2052 reviews)
Red Bricks & Blue Views Scavenger Hunt
Downtown, Annapolis, Maryland
History comes alive around every corner in beautiful Annapolis! Explore charming streets,...
5.0 (75 reviews)
Downtown Annapolis Ghost Tour
Downtown, Annapolis, Maryland
Discover Downtown Annapolis on a self-guided, app-led ghost tour packed with riddles,...
5.0 (68 reviews)
Quiet Waters Park: Hunt Through the Wild & Wonderful Scavenger Hunt
Downtown, Annapolis, Maryland
Unlock the secrets of Quiet Waters Park! Hunt through scenic overlooks, fairy trails, dog...
5.0 (66 reviews)
Annapolis Maryland Bar Hunt
Downtown, Annapolis, Maryland
Discover Annapolis through a self-guided, gamified bar crawl featuring trivia, photo...
5.0 (62 reviews)
United States Naval Academy Hunt
United States Naval Academy, Annapolis, Maryland
Anchors aweigh for laughs and discoveries! Our scavenger hunt cruises through Annapolis...
5.0 (65 reviews)
St. John's College Hunt
St. John's College, Annapolis, Maryland
Experience a self-guided, app-led St. John's College (MD) tour with trivia, photo...
5.0 (67 reviews)
Turning Pages at St. John’s
St. John's College, Annapolis, Maryland
Experience a self-guided, app-led St. John's College tour in Annapolis with trivia, photo...
5.0 (227 reviews)
Severna Park: Stroll Goals Scavenger Hunt
Downtown , Severna Park, Maryland
Enjoy a self-guided Downtown tour in Severna Park with an app-led scavenger hunt featuring...
An Epic Annapolis, Maryland experience
How Our Annapolis, Maryland Outdoor Activities Work
Our expert team researches must-see spots and secret gems across 3,050+ cities—including over 50 outdoor experiences throughout Southeast—to create unforgettable adventures tailored just for you.
During each activity your group explores on foot: answering trivia at historical markers discovering murals via photo tasks solving puzzles at public art installations—and tracking progress through our award-winning app where points unlock achievements citywide.
1
2
3
Top Outdoor Attractions In Annapolis
Annapolis bursts with charm at every corner—from the storied halls of the United States Naval Academy to the bustling energy of Main Street and St. John's College campus. Outdoor activities let you immerse yourself in centuries-old architecture, lively markets, scenic riverside paths, and buzzing local hotspots like craft breweries and live music venues. Every attraction offers a fresh perspective on what makes this city unforgettable. Click on each location to see related activities.
1
Maryland State House
Discover the State House, a must-see in Annapolis. It's iconic dome and historic brickwork tell tales of Maryland's past. Wander the grounds and feel the echoes of history in this Chesapeake Bay getaway.
2
Middleton Tavern
Step outside Middleton Tavern, a historic haunt since 1750. Imagine sailors sharing tales over crab feasts, with whispers of Blackbeard lingering at dusk—a true Annapolis attraction.
3
Susan Campbell Park
Stroll through Susan Campbell Park along Spa Creek. Enjoy panoramic harbor views and watch artists capture the morning light—a perfect outdoor activity in this Mid-Atlantic coastal charm.
4
Liberty Bell
Stand before the US Naval Academy entrance on Prince George Street. Imagine marching bands echoing through history—an essential stop for those exploring Maryland's capital city.
5
Ego Alley
Discover the Old Treasury, built in 1736 as Annapolis' oldest public building. It's weathered stone tells tales of colonial charm—a fascinating stop on your sightseeing tour.
6
Banneker-Douglass Museum
Explore Black history at the Banneker-Douglass Museum. Vibrant art celebrates Marylanders' impact—an inspiring visit during your day trip to this historic downtown area.
7
Historic Main Street
Wander Colonial Annapolis Historic Downtown’s Main Street. Discover picturesque architecture and local shops—a delightful experience capturing Mid-Atlantic coastal charm.
8
Visitor Center
Explore the Annapolis Maritime Museum, a gem for outdoor enthusiasts. Nestled by the Chesapeake Bay, it offers stunning views and insights into the city's maritime heritage. Perfect for a day trip!
9
Cartop Boat Launch Pier on Harness Creek
Quiet Waters Park is an outdoor haven in Annapolis. Enjoy scenic trails, art galleries, and live music events. Ideal for a peaceful day out in nature with family or friends.
10
South River Overlook / Promenade
Stroll around the Maryland State House grounds, where history meets beauty. This iconic site is perfect for outdoor exploration while soaking in Annapolis' colonial charm.
11
Dog Beach & Children’s Playground
Ego Alley is a lively spot for outdoor activities in Annapolis. Watch boats glide by as you enjoy waterfront dining and vibrant street performances along this bustling marina.
12
Fairy House Trail & Native Plant Garden
The William Paca House & Garden offers a serene escape with it's lush landscapes and historical insights. It is an ideal spot for those seeking outdoor beauty and cultural enrichment.
13
Bancroft Hall
Step outside and feel the Chesapeake Bay breeze as you explore Annapolis, Maryland's Capital City. Locals say you can spot blue herons along the Severn River—an outdoor treat for any day trip.
14
Buchanan House Sailor Statue
Wander through leafy streets where crab feasts echo in the air. Outdoor activities here blend Mid-Atlantic coastal charm with Naval Academy Town energy—locals recommend sunset walks by the docks.
15
Mahan Hall
Enjoy a gentle stroll along Severn River tours, where locals wave from sailboats. Outdoor things to do abound in this crab feast destination—catch glimpses of Maryland's Capital City from every angle.
16
Alumni Hall
Experience Annapolis' outdoor spirit with breezy walks near historic landmarks. Locals love spotting ospreys overhead—a true Chesapeake Bay getaway for those seeking fresh air and local color.
17
Nimitz Library
Soak up Mid-Atlantic coastal charm as you wander outdoor spaces where history meets fun. Locals whisper about secret garden corners—ideal for relaxing after a day of exploring Maryland's capital.
18
Temple Bell
Breathe in salty air while tracing Annapolis' shoreline trails. Outdoor enthusiasts love the blend of city buzz and natural beauty—a recommended way to view Annapolis like a true local.
19
Louis L Goldstein
Step outside and soak up Annapolis's Mid-Atlantic coastal charm. Discover hidden murals, hear the echo of boat horns, and catch the scent of crab feasts drifting from the waterfront. Locals say sunrise here is magic.
20
McDowell Hall
Enjoy outdoor adventures in the Sailing Capital. Stroll by historic facades, spot blue herons near the Severn River, and watch sailboats glide by. Locals know the best crab rolls are found steps from the docks.
21
Mellon Hall
Breathe in salty air as you explore Chesapeake Bay Getaway trails. Locals love picnicking under old oaks while watching regattas on the water—a perfect way to experience Annapolis's outdoor spirit.
22
Buchanan House Sailor
Take in Annapolis's historic downtown—outdoor patios buzz with laughter, and street performers add flair. Locals hint that twilight brings out the best Mid-Atlantic coastal charm for explorers.
23
St. Johns College Alumni Veterans Memorial
Naval Academy Town offers riverside walks with views of passing yachts and echoes of maritime tradition. Locals suggest timing your strolls to catch sunset colors over the Severn River.
24
The Tripoli Monument
Explore Colonial architecture framed by blooming gardens and hear stories whispered by ancient bricks. Outdoor enthusiasts love spotting osprey nests along riverside paths—a true Annapolis adventure.
25
Louis L. Goldstein Statue
26
Campus Bookstore
27
Greenfield Library
28
Maryland State House
29
Women's Rights Movement Plaque
30
Fleet Admiral Halsey Statue
31
Stan & Joes Saloon
Explore the Annapolis City Dock, a vibrant hub for outdoor activities. Enjoy waterfront views and live music as you stroll along this must-see Chesapeake Bay getaway.
32
Castlebay Irish Pub
Discover the United States Naval Academy, a key Annapolis attraction. Take a guided tour to learn about it's rich history and enjoy the stunning architecture in this Naval Academy Town.
33
DRY 85
Visit the Maryland State House, where history comes alive. This Colonial Maritime Town landmark offers fascinating insights into Maryland's past amidst beautiful architecture.
34
Galway Bay Irish Restaurant and Pub
Quiet Waters Park is perfect for outdoor things to do in Annapolis. Enjoy scenic trails, art galleries, and serene views of the Severn River Tours.
35
Boatyard Bar & Grill
Stroll along Ego Alley, where you can view Annapolis from a unique perspective. Watch boats glide by as you soak up the Mid-Atlantic Coastal Charm.
36
Red Red Wine Bar + Bistro
Explore Historic London Town and Gardens for outdoor activities that blend nature with history. Wander through lush gardens and discover colonial-era buildings.
37
Dock Street Bar and Grill (Old Annapolis Jail)
Step outside and feel the Chesapeake Bay breeze as you explore Annapolis's historic streets. Locals whisper about the ghostly echoes near Maryland's Capital City, a must-see for fans of outdoor chills.
38
Middleton Tavern
Experience outdoor thrills in this Colonial Maritime Town, where every corner holds a story. At dusk, the air tingles with tales from Annapolis's past—locals say some shadows never leave.
39
Waterfront Warehouse
Stroll under lantern-lit streets in Maryland's Capital City, where ghost stories mingle with salty air. Locals claim you can hear whispers from centuries past on quiet nights outdoors.
40
James Brice House
Enjoy an outdoor adventure along the waterfront, where Mid-Atlantic Coastal Charm meets local legend. Some say the best crab feasts happen right here—if you know who to ask.
41
Galway Bay Irish Pub
Take in the sights of Historic Downtown Annapolis while searching for traces of it's haunted legacy. The brick-lined paths are perfect for a gentle evening stroll full of intrigue.
42
The Maryland Inn
Breathe in crisp bay air as you wander past landmarks tied to Naval Academy Town lore. Outdoor explorers may catch glimpses of figures said to linger from Annapolis's storied history.
See our Top Outdoor Activities By Neighborhood
Each neighborhood in Annapolis has it's own character—think cobblestone lanes downtown, riverfront views by Eastport, or quaint colonial squares near Maryland Avenue. These areas set the stage for memorable outdoor experiences that bring friends and families together. Click on these neighborhoods to see the related activity.
Top Rated
5.0 (1 reviews)
Downtown
Downtown, Annapolis, Maryland
Downtown Annapolis offers a unique blend of history and modern charm. Visit the Banneker-Douglass Museum or stroll through Colonial Annapolis Historic Downtown. It is a...
5.0 (1 reviews)
Downtown
Downtown, Annapolis, Maryland
Downtown Annapolis is a top attraction for those visiting the Sailing Capital. From the Visitor Center to scenic overlooks, it offers unique things to do. Experience the...
5.0 (1 reviews)
United States Naval Academy
United States Naval Academy, Annapolis, Maryland
The United States Naval Academy neighborhood is Annapolis at it's most iconic. Stroll past the John Paul Jones Crypt and Nimitz Library, soaking in Maryland's capital...
5.0 (1 reviews)
St. John's College
St. John's College, Annapolis, Maryland
Discover why St. John's College is one of Annapolis's top attractions. From the Tripoli Monument to Mellon Hall, every corner reveals stories from Maryland's Capital...
5.0 (1 reviews)
St. John's College
St. John's College, Annapolis, Maryland
Explore St. John's College, where Annapolis history meets lively campus energy. From the Louis L. Goldstein Statue to the Campus Bookstore, every corner offers something...
12,000+ Reviews For our Hunts
See what people say about our outdoor activities in Annapolis
Our outdoor activities in Annapolis have earned five-star reviews from locals and visitors alike! Guests rave about how much fun they had exploring hidden gems and top attractions—one happy customer said it was 'the best day trip ever.' Join thousands who trust us for unforgettable adventures throughout Maryland's capital city.
This scavenger hunt was such a unique thing to do in Annapolis. We found beautiful murals and learned so much along the way.
Brian W.
A great walking tour that highlighted all the best parts of downtown Annapolis. I can't wait to do more hunts like this one!
Megan L.
What an incredible experience! We discovered so many cool places we never knew existed in our own backyard, even as locals.
Daniel H.
Exploring the US Naval Academy through this interactive tour was unforgettable. So many interesting points of interest around downtown!
Laura M.
FAQs.
LOCAL INSIGHTS
Fun Annapolis Facts and Hidden Gems
Annapolis began it's story as a colonial port town in 1649 before becoming Maryland's capital—a hub for sailing culture that attracts adventurers worldwide.
Locals love sharing tales about crab feasts along Ego Alley or secret tunnels beneath historic buildings! There is always something surprising waiting around each corner when visiting Ann
Locals love sharing tales about crab feasts along Ego Alley or secret tunnels beneath historic buildings! There is always something surprising waiting around each corner when visiting Ann
© 2016-2026 Let's Roam, LLC. Let’s Roam® is a registered trademark. All Rights Reserved.
✕
Valentine's Day Flash Sale: Up to 55% off all tickets and passes
Hey! Sorry to interrupt.
We’re Charlie and Mike, founders of ScavengerHunt.com
Want an extra 10% Off Your Order?
NO, CONTINUE SHOPPING
Unlock your extra 10% off your first order!
Final step to get your extra 10% off!
Sign up for email & texts to get your code
MAYBE LATER
