5.0
(10)
132
hikers
8
hikes
Urban hiking trails in Sandy Point State Park offer diverse landscapes, including sandy beaches, woodlands, and coastal terrain along the Chesapeake Bay. The park encompasses 786 acres, providing varied environments for exploration. Trails often meander through old-planted pine forests and lead to marshes, offering opportunities to observe local flora and fauna. The terrain is generally low-lying, with minimal elevation changes, making it suitable for accessible urban walks.
Last updated: May 29, 2026
5.0
(1)
13
hikers
2.88km
00:45
10m
10m
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.
7
hikers
7.97km
02:03
40m
40m
Moderate hike. Good fitness required. Easily-accessible paths. Suitable for all skill levels.

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3
hikers
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.
9
hikers
3.18km
00:49
20m
20m
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.
6
hikers
5.31km
01:23
40m
40m
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.
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The Maryland State House in Annapolis is the oldest U.S. legislative building still in active use for legislative purposes. Construction began in 1772 and took until 1797 to complete. Its striking feature is its large wooden dome—built entirely without nails. The U.S. Congress of the Confederation met here between 1783 and 1784. Today, the building is located on the grounds of Fort Williams Park and is managed by the State House Trust.
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The Annapolis boardwalk, located at City Dock, is a historic waterfront promenade that offers great views of the Chesapeake Bay. You can watch boats navigate the harbor, dine at nearby restaurants, and attend seasonal festivals and parades that celebrate Annapolis's rich nautical heritage.
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The 6th Street Bridge, also known as the Spa Creek Bridge, is a drawbridge that takes you across Spa Creek. There is a sidewalk for pedestrians to safely cross the bridge and get great views of Spa Creek.
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The Kunta Kinte-Alex Haley Memorial in Annapolis, Maryland, is the only U.S. memorial that commemorates the actual name and arrival location of an enslaved African Kunta Kinte. The memorial features a bronze sculpture of author Alex Haley reading to three children of diverse backgrounds, along with a Story Wall and Compass Rose, all symbolizing the enduring strength of African heritage and the importance of family history.
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Located at the U.S. Naval Academy, the Herndon Monument is a 21-foot-tall grey granite obelisk. It stands in honor of Captain William Lewis Herndon, who lost his life evacuating passengers during the SS Central America sinking on September 12, 1857. A nearby ship rescued women, children, and many men during the storm, preserving their lives.
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Built in 1772, Maryland State House is the oldest state house that's still in use. It is a beautiful building, topped with the largest wooden dome in the US constructed without nails. It's a designated National Historic Landmark.
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The docks are a wonderful stop on a bike trip. Historic buildings hug the water of Chesapeake Bay and boats come and go from the harbor. There are lots of eateries to refuel and shops to browse through. The docks have hosted town merchants for over 350 years.
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Established on 10 October 1845, the Naval Academy is the second oldest of the five U.S. service academies, and educates officers for commissioning primarily into the United States Navy and United States Marine Corps. The campus including the Chapel, the Memorial Hall and the impressive Dahlgren Hall can be visited, e.g. by way of historical walking tours (90 mins). https://navalacademytourism.com/historical-walking-tour?hsLang=en https://en.wikipedia.org/wiki/United_States_Naval_Academy#Halls_and_principal_buildings
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This guide features 5 urban hiking trails in the vicinity of Sandy Point State Park, primarily exploring the historic city of Annapolis. These routes offer a mix of easy and moderate walks, perfect for discovering the urban landscape.
The urban hikes in this guide, centered around Annapolis, feature mostly paved paths, sidewalks, and historic streets. You'll experience minimal elevation changes, making them suitable for leisurely strolls through the city's charming districts.
Yes, many of the urban trails are family-friendly, offering easy walks through historic Annapolis. The routes are generally short and accessible, providing a great way to explore the city's sights with children. For example, the Annapolis City Dock – Maryland State House loop from Annapolis is an easy option.
Yes, dogs are generally welcome on leashes on public sidewalks and parks in Annapolis. However, always check local regulations and signage for specific areas or establishments you might pass through. Many outdoor cafes in Annapolis are dog-friendly.
The urban hikes in this guide will lead you past significant historical and cultural landmarks in Annapolis. You can expect to see the iconic Maryland State House, the bustling Annapolis City Dock, and the Commodore John Barry Monument. The Maryland State House – Annapolis City Dock loop from Annapolis is a great way to experience many of these sights.
All the urban hiking routes featured in this guide are circular, allowing you to start and end your journey at the same point. This makes planning your walk convenient and straightforward. Examples include the Annapolis City Dock – 6th Street Bridge loop from Annapolis.
Spring and fall offer the most pleasant weather for urban hiking in Annapolis, with comfortable temperatures and beautiful scenery. Summer can be warm and humid, while winter can be chilly, but the city's charm is present year-round. Consider visiting during a local festival for an enhanced experience.
Annapolis offers various parking options, including metered street parking and several public parking garages, especially around the City Dock area. It's advisable to check the City of Annapolis website for current parking availability and rates, particularly during peak tourist seasons.
The urban hikes in the Annapolis area are highly rated by the komoot community, with an average score of 4.95 out of 5 stars. Reviewers often praise the historical charm of Annapolis, the scenic waterfront views from the City Dock, and the ease of exploring the city's landmarks on foot.
Yes, Annapolis is well-known for its vibrant culinary scene. The urban hiking routes in this guide pass through areas with numerous cafes, restaurants, and pubs, especially around the City Dock and Main Street. You'll find plenty of opportunities to stop for a meal, a coffee, or a refreshing drink.
The urban hiking trails in this guide vary in length, ranging from approximately 4.4 kilometers (2.7 miles) to 7.9 kilometers (4.9 miles). This allows you to choose a route that fits your desired walking duration and fitness level.
Yes, Annapolis has a local bus service (Annapolis Transit) that can help you get around the city. Many of the urban hiking routes start and end near central locations that are accessible by public transport. Additionally, the city is walkable, making it easy to reach trailheads once you're in the downtown area.


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