Discover the Best Hiking Near Annapolis, Maryland

Located on the scenic shores of the Chesapeake Bay, Annapolis itself offers modest green spaces but is not a hub for traditional hiking. However, the surrounding region pulses with opportunities for hikers eager to leave the city’s historic streets and engage with Maryland’s diverse landscapes. While Annapolis serves as your gateway, the true hiking adventures unfold just beyond city limits within a short drive.

Expect trails that challenge your steps and inspire your senses along wooded ridges, marsh-bordered paths, and gently rolling hills. Many routes accommodate both newcomers to the trail and seasoned backpackers looking for a quick day escape from urban life.

In planning your trek, keep practical details top of mind: trail lengths from 2 to 8 miles accommodate varying levels of fitness, and terrain ranges from flat woodland paths to moderate inclines that push your endurance. The natural environment is alive, with rivers daring you closer, and wildlife quietly observing your passage through their domain.

Hydration is critical, especially from late spring through early fall when Maryland’s summers bring humidity. Durable footwear with good traction is necessary, as paths can turn slippery after rain or morning dew. Early morning or late afternoon hikes offer comfortable temperatures and blend the day’s changing light with the quiet pulse of nature.

For more specific recommendations, our full listings of the best adventures in Annapolis, Maryland below will guide you to detailed trail descriptions, maps, and tips. Whether you are seeking a quick walk to reset or a full afternoon trek, nearby hiking spots provide a practical yet invigorating escape.

Embrace the challenge as a shared venture with the landscape — a force of nature fiercely itself, not unlike your own adventure spirit. Step beyond Annapolis and find the trails calling you to measure your strength and soak in Maryland’s scenic beauty.