Looking for the best trails around Culpeper?

Explore the best rated trails in Culpeper, VA, whether you're looking for an easy walking trail or a bike trail like the Meadowlark Connector Trail and Ox Road Sidepath . With more than 40 trails covering 285 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.

Recent Trail Reviews

Rocky Run Stream Valley Trail


April, 2024 by zxdf4q96ty

Very calming trail with little to no traffic at 7pm.

Washington and Old Dominion Railroad Regional Park (W&OD)

Great trail, watch out for speeding cyclists

March, 2024 by peter.ortizmarrero

Only did part of the trail from Herndon to Reston. Just watch out for the ‘Lance Armstrong’ wanna bees. Most of them do alert they are coming to your left, so stay to your right and you should be ok.

Gerry Connolly Cross County Trail (VA)

can’t even find parking

February, 2024 by gnorthpiegan

The map gave us the start of the trail. But, it was in a neighborhood and there was no parking at all.


Dahlgren Railroad Heritage Trail


December, 2023 by zx8q54srfm

As others have said - this trail is very bumpy. Much of the trail still has railroad ties going across it. I did on a touring bike and even deflated the tires partway into the trail. I still called it after 8 miles. Just not much fun. Hope they will improve it a bit sometime because I lived the countryside and overhanging tree branches etc. Really beautiful. Good walking trail or mountain bikes.

Railroad Ford Trail

closed for Bridge repairs

November, 2023 by dalemccleese

Closed for Maintenance

Washington and Old Dominion Railroad Regional Park (W&OD)

Washington and Old Dominion Railroad Regional Park

November, 2023 by thejake91739

I started my experience at the trailhead of the charming and historic town of Purcellville at 7:30 on a Saturday morning in late October. I only went about six miles, but was surprised at the amount of fitness minded people using the trail so early in the day. It was primarily walkers and runners, but every now and then serious speed demons on their bikes would race past me. It's certainly a good trail for building up speed.

As for me, a tourist from California, I was moving along the trail moderately so as to take advantage of as many photo ops as possible. I especially enjoyed the fall colors, rolling hills of farm and pasture land, and some historic, vintage buildings. The stately country homes were absolutely stunning! I wish I'd had more time to explore more of this trail further!

Gerry Connolly Cross County Trail (VA)

Why are the signs so unclear?

September, 2023 by 445kim

All I wanted to do was get from the Springfield Metro Station to Springfield - by Sydenstricker/Rolling Road. It's really unclear (or at least on both my GPS apps) on how to get back. Bike baths just kept ending and there was no sign (that I could see) indicating an alternate path, I had to weave thru neighborhoods guessing - but again w/no real signs and sometimes it just felt like it kept leading me again and again to the parkway. A few more signs, a bit more clarity. I've never struggled with a path so much and I bike all over MD, DC and VA. I seriously went around in circles around Hooes and Rolling for over 1.5 hours. I finally just biked on the emergency lane on the Parkway to get to Backlick.

Washington and Old Dominion Railroad Regional Park (W&OD)

Too many road cyclists going way too fast! This is a trail not a road. So watch out if you want to leisurely ride your bike on this trail because they are flying by.

August, 2023 by carlalger.50

Too many road cyclists going way too fast! This is a trail not a road. So watch out if you want to leisurely ride your bike on this trail because they are flying by.

Indian Head Rail Trail

Just off Highway 301

August, 2023 by mackbrazelle

Flat long (13 miles) and smooth. Take a break from the traffic and go for a ride.

Dahlgren Railroad Heritage Trail

Currently Recommend Mountain Bikes Only

July, 2023 by rgbarch330

Four of us ONLY rode this trail between rte 605 (Western End Trailhead Parking) eastbound to rte 609 (crossing/Trailhead Parking) and return. Found many exposed tree roots, hazardous rusting railroad tracks, perpendicular decaying railroad ties and loose gravel resulting in a very bumpy and stressful ride. (With proper funding, this trail has enormous potential). Considering this Rails to Trail’s current condition, I would not use a road bike or trike and would be very cautious with a hybrid . I’d highly suggest a mountain bike with front fork suspension on Dahlgren Trail, considering it’s current condition! It’s has the potential to be an awesome 15+ mile Rail Trail!

Dahlgren Railroad Heritage Trail

careful directions at the church

July, 2023 by ib123

I started midway and headed east. The detour puts you out behind the church (2 miles before the Sheets endpoint) and then you're on your own. I went to the main road then took a right back towards where the trail was and never found it. I thought the Karoo was confused because of the detour. If I could zoom out on the karoo I'd have seen the route turns at the gate behind the church. Just check the map for this detail before embarking. the bumps aren't as bad as I was lead to believe, actually below standard bumpiness. The gravel is pea gravel, a bit thick in stretches so it slows you a bit. 2 deer 2 blue herons, 1 box turtle in 18 miles round trip.

Saunders-Monticello Trail

Not Rail Trail

June, 2023 by resifence

Beautiful Trail 270' up in 2 miles if you're in shape stunningly beautiful 2 miles.

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