Crank up your sense of adventure by exploring Annapolis Scavenger Hunt experiences throughout downtown hotspots like United States Naval Academy Scavenger Hunt or St. John's College Scavenger Hunt—uncovering street art bursts, charming alleys, buzzing plazas, and more.
Gather your group for trivia quests, daring photo dares, and wild challenges—all tracked in our app so you can rack up points and celebrate victories together after a day spent conquering Outdoor Activities in Annapolis!
Top Outdoor Activities In Annapolis, Maryland
Step into the vibrant heart of Annapolis, Maryland's Capital City, where cobblestone streets meet sparkling waterfronts and history comes alive around every corner. Outdoor activities in Annapolis offer an unforgettable way to view Annapolis from fresh perspectives, whether you are a visitor or a local. From the bustling Historic Downtown to scenic college campuses, our outdoor experiences reveal must-see sights and hidden gems alike. Get ready for adventure as you discover why these activities are among the top things to do in Annapolis.
Adventurers exploring in Annapolis!
Outdoor Experiences in Annapolis, Maryland
Welcome to our expertly curated collection of outdoor activities in Annapolis! Each experience is designed for maximum excitement—think lively tours through legendary neighborhoods, creative challenges at iconic landmarks, and unexpected twists that keep everyone engaged. Whether you crave family friendly fun, love art galleries and historic sites, or seek unique outdoor activities with friends, there is something here for every explorer. Dive into each activity below and uncover new ways to make the most of your day trip or sightseeing adventure.
Top Rated
5.0 (2204 reviews)
Maritime Matrix Maryland Mode Scavenger Hunt
Downtown, Annapolis, Maryland
History comes alive around every corner in beautiful Annapolis! Explore charming streets,...
5.0 (128 reviews)
Downtown Annapolis Ghost Tour
Downtown, Annapolis, Maryland
Discover Downtown Annapolis on a self-guided, app-led ghost tour packed with riddles,...
5.0 (78 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 (68 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 (66 reviews)
Annapolis Maryland Bar Hunt
Downtown, Annapolis, Maryland
Discover Annapolis through a self-guided, gamified bar crawl featuring trivia, photo...
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 (268 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 cities worldwide—including over 50 Outdoor Activities across Southeast—to craft immersive routes featuring must-sees and secret finds tailored just for each destination like Annapolis. Every activity includes clear instructions plus challenge quizzes designed specifically around local culture.
During each experience your team explores on foot: answer trivia at historical markers downtown; snap photos by colorful murals; solve puzzles at public art sites—all earning points tracked through our award-winning app so everyone can compare scores after completing these exciting Outdoor Activities.
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Save up to 54% on Annapolis Top Sights
One digital Top Sights Pass bundles admission to your choice of Annapolis attractions plus one Let's Roam city adventure. Choose 3, 4 or 5 experiences in total: one city adventure and the rest attractions you pick after purchase. Browse the included attraction options below.
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Annapolis Harbor & USNA Cruise — Harbor Queen
See Annapolis Harbor from the Harbor Queen on a narrated boat cruise. The route passes the banks of the U.S. Naval Academy and introduces the city's history as a seaport, its waterways and views toward the Chesapeake Bay Bridge. This is a seasonal cruise with scheduled departures, not year-round harbor transportation. Confirm the sailing date and current boarding location before your visit.
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William Paca House and Garden
Tour the 1760s Georgian home of William Paca, a signer of the Declaration of Independence, then explore its restored two-acre garden. Period furnishings and paintings provide context for life in Revolutionary-era Annapolis. Outside, formal garden areas, a kitchen garden, a pond and the Summerhouse create a different side of the visit. House tours and seasonal opening hours should be checked in advance.
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Colonial Annapolis & Maryland State House Tour
Follow a colonial-attired guide through Annapolis's historic district and visit the Maryland State House. The walk connects eighteenth-century streets and homes with major events, including George Washington's resignation of his military commission and ratification of the Treaty of Paris. Adult guests must bring the required physical photo identification for State House access. Check the scheduled departure and meeting point before joining the tour.
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Watermark Historic Ghost Tour
Hear Annapolis ghost stories on a guided evening walk through the historic district. A period-attired guide shares dramatic accounts connected to the city's old streets and buildings, with the route finishing at St. Anne's cemetery. The emphasis is on storytelling rather than staged scares. Tours operate on selected seasonal dates, so confirm availability instead of assuming a departure every evening.
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Museum of Historic Annapolis
Discover more than four centuries of local history at the Museum of Historic Annapolis on Main Street. Three floors of exhibitions, objects and a film introduce the diverse people who helped shape the city and its place in the national story. The standard visit is self-guided. Guided introductions may be available separately, and seasonal opening days vary.
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Chesapeake Children's Museum
Chesapeake Children's Museum is a play-based museum for young children and the adults who explore with them. Its exhibits connect hands-on discovery with the culture and natural setting of the Chesapeake region. Plan for an interactive family visit rather than a traditional gallery tour. Check the museum's program and opening information for the day you intend to visit.
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Top Outdoor Attractions In Annapolis
Annapolis is packed with attractions that shine brightest when explored outdoors. Stroll past the stately grounds of the United States Naval Academy, take in colonial charm along Main Street, or hunt for murals tucked away near St. John's College. The city's vibrant marina buzzes with energy while historic plazas invite you to linger and soak up Chesapeake Bay breezes. These recommended outdoor activities let you experience Annapolis like never before—full of color, culture, and surprises at every turn. 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
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.
4
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.
5
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.
6
Thurgood Marshall
Step outside and soak up Annapolis's Mid-Atlantic Coastal Charm. Enjoy the fresh Chesapeake Bay breeze and watch sailboats glide by—a true Crab Feast Destination vibe for your outdoor adventure.
7
Hammond-Harwood House Museum
Experience the Chesapeake Bay Getaway vibe as you stroll by this spot, where Annapolis's maritime charm shines. Feel the breeze and watch boats glide by—locals say sunsets here are unforgettable.
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
Step out and explore Annapolis as the Chesapeake Bay breeze guides you past vibrant murals and historic brick lanes. Locals say the best crab feasts happen right on the docks—bring your sense of adventure!
26
Campus Bookstore
Wander through Annapolis where outdoor art pops up in unexpected corners and the Severn River sparkles nearby. Locals love spotting blue herons at sunrise—an authentic Chesapeake Bay getaway moment.
27
Greenfield Library
Enjoy Annapolis attractions outdoors—watch sailboats race or catch a street performer near the Naval Academy. Insiders know sunset here paints the city in golden hues, perfect for sightseeing.
28
Maryland State House
Take a day trip to Annapolis and stroll it's leafy parks, where locals picnic under centuries-old oaks. The city’s crab feast destination status is legendary—outdoor tables fill fast during weekends.
29
Women's Rights Movement Plaque
Outdoor things to do abound in this East Coast sailing hub—think riverside walks, public art, and breezy plazas alive with laughter. Locals recommend watching boats parade by on festival days.
30
Fleet Admiral Halsey Statue
Annapolis invites you outside: trace colonial brickwork, spot quirky weather vanes, or relax by the water’s edge. Local trivia: some alleys still follow 18th-century property lines—history beneath your feet!
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
Discover outdoor adventures woven into the fabric of Annapolis' most beloved neighborhoods—from lively Historic Downtown to the serene Severn River banks. Each spot offers it's own blend of local flavor and must-see experiences that will inspire your next outing—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
Thousands have trusted us for their outdoor adventures in Annapolis—and they cannot stop raving! One happy customer called it 'the best way to see hidden corners.' With glowing star ratings across top platforms, our outdoor activities consistently earn high praise for creativity and fun. Join fellow explorers who have made memories with us all over 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 was founded in 1649 by Puritan exiles from Virginia seeking religious freedom—it quickly became Maryland's capital city thanks to it's strategic Chesapeake Bay location.
The city has hosted everything from colonial assemblies to world-famous crab feasts! Did you know locals call it 'Sailing Capital' because it draws boaters from all
The city has hosted everything from colonial assemblies to world-famous crab feasts! Did you know locals call it 'Sailing Capital' because it draws boaters from all
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