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Routes
Bike touring routes & trails
United States
Maryland
Queen Anne'S County

School Days Trail

Moderate

2.8

(3)

97

riders

School Days Trail

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:

Wye Mills Fish Management Area

Waypoints

A

Start point

Parking

Get Directions

1

28.4 km

Little Red Schoolhouse

Highlight • Historical Site

This beautiful little school is the only one still standing of the more than forty that were similar. It was in use until the late 1960s.

Tip by

2

39.6 km

Wye Mill

Highlight • Historical Site

Cycling alongside Wye Mill takes you back in time to think about the history of this area, how these mills operated and how the industry developed here.

Tip by

B

39.6 km

End point

Parking

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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

Elevation

Nothing selected – click and drag below to see the stats for a specific part of the route.

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Weather

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Today

Saturday 23 May

14°C

10°C

98 %

Additional weather tips

Max wind speed: 23.0 km/h

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This route was planned by komoot.

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Frequently Asked Questions

What is the best time of year to cycle the School Days Trail?

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.

How long does it typically take to complete the route?

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.

Is the trail suitable for beginner cyclists?

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.

What kind of terrain can I expect on the route?

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.

Where can I park to access the School Days Trail?

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.

Are there any notable landmarks or points of interest along the way?

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.

Is the School Days Trail dog-friendly?

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.

Do I need a permit or pay an entrance fee for this trail?

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.

What kind of scenery will I experience on this cycling route?

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.

Are there any specific safety considerations for cyclists on the trail?

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.

Is the School Days Trail a loop route?

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.

Nearby routes

Moderate

2.5

1

School Days Trail

02:20h

39.6km

90m

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