2.8
(3)
97
riders
02:20
39.6km
90m
Cycling
Embark on the School Days Trail for a moderate touring cycling experience across Talbot County's flat, expansive farmland. This route spans 24.6 miles (39.6 km) with a gentle elevation gain of 304 feet (93 metres), making for a pleasant ride that typically takes about 2 hours and 19 minutes. You…
Last updated: April 23, 2026
Tips
Your route passes through a protected area
Please check local regulations for:
Waypoints
Start point
Parking
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28.4 km
Highlight • Historical Site
Tip by
39.6 km
Highlight • Historical Site
Tip by
39.6 km
End point
Parking
Way Types & Surfaces
Way Types
19.8 km
18.7 km
1.10 km
Surfaces
21.9 km
14.1 km
3.58 km
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Elevation
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Weather
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Today
Saturday 23 May
14°C
10°C
98 %
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Max wind speed: 23.0 km/h
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This route was planned by komoot.
The trail is enjoyable throughout the warmer months. Spring and fall offer pleasant temperatures and beautiful scenery, with changing seasonal views of farmland. Summer is also suitable, but be prepared for warmer weather.
The route is approximately 39.5 kilometers (24.5 miles) long. For touring cyclists, it typically takes around 2 hours and 20 minutes to complete, depending on your pace and stops.
Yes, the School Days Trail is generally considered suitable for cyclists of all skill levels, including beginners. It features relatively flat terrain and is mostly paved, making for a pleasant touring cycling experience.
You can expect mostly flat terrain, winding through expansive farmland. The majority of the surfaces are paved, offering a smooth ride. However, be aware that one specific section, Glebe Road, has no shoulder and deep ditches, requiring extra caution.
While specific parking locations are not detailed, the trail is located in Talbot County, Maryland, which offers various access points. It's advisable to check local resources or the komoot tour page for recommended starting points and parking options near the route.
Yes, the route features several historical sites. A key highlight is the historic Little Red Schoolhouse in Longwoods. You will also pass by Wye Mill, another significant historical site. The trail also offers glimpses of the Chesapeake Bay and opportunities for nature viewing near the Pickering Creek Audubon Center.
Generally, cycling trails in rural areas like Talbot County are dog-friendly, especially if your dog is accustomed to riding in a trailer or running alongside a bicycle. However, always ensure your dog is on a leash and that you clean up after them. Check local regulations for any specific restrictions at historical sites or nature centers along the route.
No, there are no permits or entrance fees required to cycle the School Days Trail itself. It is a public route through Talbot County's scenic landscapes.
The route offers classic Eastern Shore scenery, characterized by sprawling farmland and "big sky" vistas. You'll enjoy changing seasonal views, glimpses of the Chesapeake Bay, and diverse wildlife. It's a great way to experience the natural beauty and cultural heritage of Talbot County.
While the trail is generally flat and pleasant, cyclists should exercise extreme caution on the section of Glebe Road. This part of the route is noted for having no shoulder and deep ditches, so it's important to be vigilant and aware of your surroundings.
Yes, the School Days Trail is designed as a loop route, allowing you to start and end your ride at the same point without needing to retrace your path.