Explore the best rated trails in Chesapeake, VA, whether you're looking for an easy walking trail or a bike trail like the Salem Road Trail and General Booth Boulevard Trail . With more than 31 trails covering 186 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.
We only had one day to ride so rode from the Herring Creek trailhead to Jamestown and then back. We found the trail to be what most have stated previously. Signage was great, the asphalt trail was in great shape and it was not very crowded (we rode on Thursday). As other have stated there are not many facilities so pack food and water. Yes, there were some hills on that section but nothing crazy in our opinion. We gave it an "A". Would have been A+ if there had been even some port-a-johns here and there.
As stated in the last review, you cannot enter any circumstances ride the Amtrak train back to Richmond from Williamsburg with E bikes! While indeed, my wife and I managed to do that we will clearly be the last people to ever be allowed to do so. To say that it was a nightmare is a huge understatement. We expect to be inducted into the Virginia railroad museum Hall of Fame in the future as the only couple to ever ride the Virginia Trail and return with E bikes on a train. Of this, we are very proud and glad to be trendsetter such as those that sat down at the sit in the 60s in the 70s for equal rights.
The trail itself was great for our hybrid-tire bikes, and a good length. The problem is that it’s crowded with walkers, dog walkers, and joggers, many of whom don’t know how to behave on a shared-use trail. There is not a single sign about trail etiquette anywhere.
I went on a Wednesday around 1:00pm so there was no one there. The trail is perfectly paved and plenty wide.
I give it 5 stars because it is over the whole way. I rode Williamsburg to Richmond. There are very little roots coming through the pavement which is a positive Shaded for the first 30 plus miles. Plenty of parking in Williamsburg and Richmond. I missed one turn. One nice rest stop about 10 miles from Richmond I live in Chesapeake Virginia and this was very hilly for me. Constant up and down. The negatives are the lack of benches to sit. I counted 3 of them for about 40 plus miles. There was also a lack of stores. Bring you own hydration. The
The trail path is paved. This would be a good trail for training to do longer trails on a road bike. It is a safe, clean, and beautiful trail through nature. The trail is approximately 3.5 miles from end to end per my "igsport IGS360" bike computer.
We had a really nice ride...had the trail to ourselves (on a Thursday). We parked at the Welcome center and rode from there. Enjoy!!
There’s no trail, the crosswalk infrastructure is minimal and the buttons to cross don’t work
Husband and I went for the first time and it was horrible. We started biking a few weeks ago. Did not like the bike trail here. While I understand it’s a nature trail it is not for any bike. Roots sticking up out of the ground 6inches high. Your not supposed to ride bikes on the nice flat trail but we ended up doing just that. Trails for bikes are not marked well either. My husband flipped his bike on one of the hills. Will not be going back for the bike trail that’s for sure.
Wonderful paved trail where I bike and lead rides for our local trail club. Great for all level of bicyclists as its mostly flat on the Jamestown end. Led a group of 10 recently for 36 miles and had lunch at the Jamestown Settlement. It is shaded in the summer. It is one of my favorite paved trail to ride. It is also part of the Trans American Trail for going cross the country.
Sandy
The sidewalks were in disrepair, the trees were hanging too low, the traffic was unbelievable and heavy. Not one cross walk signal worked. We felt in danger most of the ride! This was a one and done for us! Prefer the Beach Boardwalk area a million percent over this madness!
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