Explore the best rated trails in Preston, MD, whether you're looking for an easy walking trail or a bike trail like the Cross Island Trail and Strawberry Lake Way Bicycle Path . With more than 43 trails covering 157 miles you're bound to find a perfect trail for you. Click on any trail below to find trail descriptions, trail maps, photos, and reviews.
The trail is paved and easy to ride, and the water fountains that line the trail actually work! Great for beginners and experienced riders. Well-populated but not overcrowded.
I just rode 28 miles round trip today (May 30, 2025) on the WB&A Trail and it was great!
Contrary to the narrative in the description, the bridge over the Patuxent River is now open.
Started in Odenton and parked on Railroad Ave just North of the trail entrance and rode all the way to Annapolis Road (Rt 450).
Lots of bikers and pedestrians out on the trail today.
Great day to ride!
The bridge is open and you're able to ride the full length of the trail. Great nature viewing throughout the ride. Surprisingly, over 1000 ft of elevation gain.
Nice trail. Parking at either end of the trail. 1 port-a-potty at the trailheads. All asphalt & level just watch for upheavals in the trail in a couple of different places.
An amazing free resource for the lower eastern shore. Flat sand trail mostly covered with pine needles. I would not recommend this trail if your tires are less than 50mm (2 inch) wide. Minimal but effective main trail markings. Multiple unmarked side trails. Adequate parking. Pack a lunch and make a day of it. This is a state forest not a park, there are port-a-john's near the parking area.
This is a really nice trail for a quick ride on any kind of bike. Really enjoyed it today wish it was longer.
We live in Milton and have visited the trail several times. Each time I think how awesome it would be if it connected to the larger trail system leading into Lewes, Cape Henlopen State Park, and Rehoboth. On occasion, we will get into the car and drive to one of those trailheads. The Milton rail trail is beautiful, but maybe be a little shortsighted for those wanting more of a workout/challenge/enjoyment.
This “trail” is nothing more than a sidewalk behind a shopping center.
I frequently ride the Cross Island Trail. You can extend your ride starting at the Royal Farms. Continue on Sadler Rd when it ends make a left on Chester River Beach Rd then right on VFW Ave. At the Quality Inn make a left onto Winchester Creek Rd. Then right onto Hissey Rd and then left back onto Winchester Creek Road. Stop at Nesbit Rd. The roads are not busy and will add 4 more miles to your round trip.
This is a well maintained trail, flat, varied scenery with a great long boardwalk/ bridge. Nice stops in a few sites with some history. Beach view / marsh / birds. Well traveled with bikers & walkers on a Sunday fall afternoon. 6.4 miles round trip with a strong wind on the way back had me sweating.
We were on Kent Island for a wedding, and we took a stroll from the Hyatt Hotel in the direction away from the Bay Bridge. The trail runs alongside the busy road for a mile or so, then there’s a short stretch in a pleasant piney woods, and then back to the busy road. The trail is well maintained and the surface is good, and the part in the woods was pretty nice. But for most of our 3.5 mile walk (total, there and back) it was like walking beside a busy road. If I did this again, I’d try to access the trail at a place where you would have a nicer experience.
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