Overlook Trail
- 0.2 mi
- round trip
- 83 ft
- climb
- Singletrack
- surface
- Out and back
- route
- Mar–Jun, Sep–Nov
- best months
Overlook Trail is a short, easy mountain biking route in Maryland, about half a mile from the community of Rolling Knolls. The trail is a 0.17-mile out-and-back, with a total climb of about 83 feet, and it's set up as a green circle for riders who want a quick, low-commitment ride. The trail's name hints at scenic viewpoints along the way, and its brief length and gentle grade make it a good choice for beginners, warm-ups or family outings. Dogs are allowed as long as they stay on a leash. Spring and fall are the most comfortable times to ride. Typical averages from a nearby weather station in Annapolis show May highs around 77°F and October highs around 68°F, while July averages climb to about 89°F. The trail sits close to several other routes. The Missing Link Connector and Honeysuckle Through Trail are each about 0.1 mile away, and the Woodland Loop and Solstice Valley Trail are about 0.2 mile off for hikers.
Local outfitters
- Terrapin Adventures17 mi away
- Blackwater Adventures Chesapeake Bay46 mi away
Not on Roamze yet. Their page has how to reach them.
Best time to go · Mar–Jun, Sep–Nov
Best time to visit Overlook Trail
Best months: March–June and September–November. Best months have typical highs of 55–85 °F, lows of 30 °F or warmer (32 °F where the station doesn't record snow), at most one snowy day and no more than 12 wet days.
Jan
44° / 29°
Feb
48° / 31°
Mar
55° / 38°
Apr
68° / 48°
May
77° / 57°
Jun
85° / 67°
Jul
89° / 71°
Aug
86° / 70°
Sep
80° / 65°
Oct
68° / 52°
Nov
58° / 41°
Dec
48° / 34°
Typical high / low (°F) and days with rain or snow, 1991–2020. Measured at Annapolis Police Brks, MD, 3.2 mi away at 25 ft. This station doesn't record snowfall. Source: NOAA NCEI U.S. Climate Normals 1991–2020.
Keep exploring — more rides worth the drive
RIDE
Overlook Trail
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Short, easy singletrack perfect for beginners and skill building in Maryland.
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Missing Link Connector
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Easy connector trail with mixed surfaces, perfect for beginners and casual rides.
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Honeysuckle Through Trail
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Short, beginner-friendly singletrack perfect for skill building and easy rides.
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Missing Link Connector
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Easy green circle singletrack connector perfect for beginners and linking trail segments.
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Woodland Loop
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Easy flowing singletrack loop through Maryland woodland, perfect for beginners.
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Solar Park Loop
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Easy 0.72-mile singletrack loop perfect for beginners and skills practice.
RIDE
Missing Link Connector
Next door
Short, easy singletrack connector perfect for beginners and warm-ups.
RIDE
Missing Link Connector
Next door
Easy connector trail with mixed surfaces, perfect for beginners and warm-up rides.
RIDE
Overlook Connector
Next door
Short, easy singletrack connector perfect for beginners and warm-ups.
RIDE
Housley Loop
Next door
Easy 1-mile singletrack loop perfect for beginners and quick rides through Maryland forest.
Map and trail data © OpenStreetMap contributors
