Milford, DE Snowmobiling Trails and Maps

345 Reviews

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Kent Island South Trail

5.8 mi
State: MD
Asphalt
Trail Image Trail Name States Length Surface Rating
The Kent Island South Trail is one of two popular recreational trails (along with the Cross Island Trail) on Maryland's Kent Island, the largest island in the Chesapeake Bay. The trail runs parallel...
MD 5.8 mi Asphalt

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Trails by activity

Kent Island South Trail

MD - 5.8 miles

The Kent Island South Trail is one of two popular recreational trails (along with the Cross Island Trail) on Maryland's Kent Island, the largest island in the Chesapeake Bay. The trail runs parallel...

Kent Island South Trail

MD - 5.8 miles

The Kent Island South Trail is one of two popular recreational trails (along with the Cross Island Trail) on Maryland's Kent Island, the largest island in the Chesapeake Bay. The trail runs parallel...

Kent Island South Trail

MD - 5.8 miles

The Kent Island South Trail is one of two popular recreational trails (along with the Cross Island Trail) on Maryland's Kent Island, the largest island in the Chesapeake Bay. The trail runs parallel...

Recent Trail Reviews

Dennis Township Bike Path

As you can see in the user contributed photo a 4 mile extension of the Middle Township path is under construction. Creating a 17 mile seamless paved path between the Dennis Township and Cold Spring (near Parkway exit 0) in Lower Township.

January, 2022 by fjohnboyle

As you can see in the user contributed photo a 4 mile extension of the Middle Township path is under construction. Creating a 17 mile seamless paved path between the Dennis Township and Cold Spring (near Parkway exit 0) in Lower Township.

Middle Township Bike Path

Partially Closed

December, 2021 by ur2bgr8

There is a chunk of the path in the Burleigh/Whitesboro area that has been closed for months for no apparent reason that I can see by looking down the path. Perhaps someone forgot to remove the signs. This forces riders to leave the path or cut their ride short. Without the closure, I’d give it 5 stars.

Kent Island South Trail

The nicely paved route parallels a busy highway. Driveways on the other side. No vistas or water views.

November, 2021 by blueheron490

The nicely paved route parallels a busy highway. Driveways on the other side. No vistas or water views.

Accordion

Cross Island Trail

Relaxing ride

November, 2021 by davidisname

I parked at the East end of Long Point park. It was just off exit 43A (RT 50 West) and right next to a Royal Farms ,however, it has only 3 parking spots. There are many more parking spots at the West end of the park. Long Point Park is a small picturesque park where you wind through the trees. For the next 1-1.5 miles you parallel Rt 50 with views of the Chester river to the North and Prospect Bay to the South before crossing under Rt50 and continuing West. You then cross the Kent Narrows Bridge and cross back under Rt50 at Piney Narrows Road where there is also more parking. Traveling West you pass through small forests, marsh, and pass by several housing developments (about 3.5miles) before making a sharp right turn into Old Love Point Park. If you turn left you enter State St and should turnaround as I did. Old Love Point Park can get congested because you are passing through a sports complex of several ball fields, tennis courts, and soccer fields with Kent Island High School in view. You must cross several roads, so be wary of traffic especially Love Point Road, It’s about another mile to Terrapin Nature Park. In the park you can take several loops and you lose the asphalt. If you take the loop that parallels the Chesapeake (after about a mile) you come to a very small bridge with the beach and the Chesapeake Bay directly in front of you. Great view of the Chesapeake and Bay Bridge !! Here the trail is all sand and I had to dismount and walk SW along the beach for approximately 200 ft before the trail was hard packed again. I then continued my ride through the trees, passing through the Cross Island Trail Trailhead parking lot and looped back to where I entered Terrapin Nature Park. I then enjoyed the ride back to Long Point Park. The ride was about 15 miles and I savored a Krispy Kreme donut at the Royal Farms when finished.

Ben Cardin C&D Canal Recreational Trail

C & D Trail

November, 2021 by prhelt

This is really a 15 mile trail 30 miles round trip. It runs from Delaware City to Chesapeake City. The Ben Cardin is the short MD part and the Michael Castle is the DE part. If it was not for a sign you would not know you were going from one trail to the other at the state line. It is well paved and in very good shape. I few good hills where it had to take a detour for one reason or another, but not many. There is a short road (More Like a Parking lot) section when you go through a marina. That is the sharp turn on the map. There is another short road section in Delaware City but only because the signs say not to ride on the sidewalk which is really the trail at that point. No traffic at either. The canal is nice, but not a whole lot to see. Worth the trip. Only 4 stars as there was not much to see but the trail itself was great. If I lived near I would ride it a lot.

Junction & Breakwater Trail

Very nice trail, beautiful woods

November, 2021 by cjkupfer

Stayed at Cape Henlopen State Park and found we could connect the park trail, into Lewes (permanent pylons separating you from light traffic into town). There we connected to the Lewes-Georgetown trail for a short bit, then crossed Hwy 1 at the library to the Junction-breakwater trail. Rode into Rehoboth, where we were able to ride the boardwalk(after season, not allowed summer), then found the Gordon’s Pond trail (after a mile or so on residential road) back into Helopen park. Ended up with about a 19-mile loop! Nice shade and forest on the Junction-Breakwater trail, which is probably great for summer, a little cool in the shade in Nov.

Bob Trail

Nice Easy Ride

October, 2021 by beachbum25

Nice Ride through a State Park, I have been here on Many Weekday Afternoons after work & it has never been crowded. Main Trail Loops around Trap Pond & through the Campground, some Boardwalk, some Stone, Some narrower riding through the woods on Stone Dust. Plenty of other areas in the Park to ride as well. Easy to get 10 Miles in just cursing around the Park. Very Enjoyable

Cross Island Trail

Nice Peaceful Ride

October, 2021 by beachbum25

Really enjoy this Trail, have ridden it several times. Well laid out, enjoyable, plenty of great spots to eat on Kent Island. Always recommend it to Friends.

Assateague Island Bike Path

Great Ride

October, 2021 by beachbum25

I have ridden this Trail many times as I live on the Maryland Shore & Go to Assateague often, I never added it here as it isn't a True Rail Trail but noticed someone had so I'll put my $.02 in. Very Flat, only hill is the Bridge over the Bay. Can be quite windy so I usually Park at Visitor Center & Ride south first as this is generally into the wind, but be sure to check the Flag when you get there as it does sometimes turn abound. Horses may be seen anywhere on the Island....you will see plenty of Horse Droppings! There are 2 Bayside Access roads which are worth a visit, there is also a Bike Trail in the State Park Campground Area that is easy to get to. It ends at a gravel Parking lot near a Construction access gate Midway down Bayberry Drive, so you can get from one Trail to the other & add some variety to your ride. No Ocean Views from the Trail but there are plenty of spots where you can stop in The National Park Campground Loops & walk up over the Dunes. Trail Ends at OSV Zone, which requires a Permit. I often Bring My Jeep & make a Day of it here, but it gets VERY Crowded on Summer Weekends. You can always Bike in even when there are Massive Summer Backups on the Road. Easy to get 10 - 15 miles in here if you get Creative.

Gordons Pond Trail

Great Scenic Ride

October, 2021 by rideforever

I loved this ride. It is a great, well maintained trail.

It is a bit of a ride from our place in Selbyville, but it is well worth the trip to to ride the trails in the Rehoboth-Lewes area and avoid the aggressive drivers in our area.

I did modify the ride a bit. I started at the beginning of the Breakwater Junction trail and rode to Lewes. I did have to ride on the road for a short distance to get over the Rehoboth-Lewes Canal to get to Cape Henlopen State Park.

If you want a longer ride, you can connect with the Lewes Georgetown rail trail. I does not go all the way to Georgetown yet, but it will be a nice long ride when it is finished.

Junction & Breakwater Trail

loved it!

October, 2021 by hepdj

This trail is really beautiful. It’s hard to believe you leave the outlet mall and 30 seconds you’re on this beautiful secluded trail! Very well maintained. It was 3.8 miles from the Tanger outlet detour entrance to Lewes.

Georgetown-Lewes Trail

Simply a beautiful and well maintained trail

September, 2021 by dfink4437

Recently relocated to the area and I couldn’t wait to explore the bike trails and learn a bit more about the area. This trail is magnificent!

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