Explore the most popular trails near Upperville with hand-curated trail maps and driving directions as well as detailed reviews and photos from hikers, campers and nature lovers like you.

Upperville, Virginia Map
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Beautiful trail. All the trails in Sky Meadows are marked clearly . The grass in the meadow areas is fairly tall so be sure to do thorough tick checks . I'd say the meadow is obviously easy but once you hit the wooded part of the trail it certainly upgrades to a moderate trail. All in all I did this with my 4 year old son and (aside from whining he was tired during the moderate incline up the mountain lol) he was able to complete it well. You will cross 2 streams ,so be prepared to get a little wet in the feet

hiking
2 months ago

Really beautiful views of farms and wildflowers! A nice switch up from regular hikes!

The trail mixes gently undulating miles through the meadow with a moderate climb to the summit of Lost Mountain. The stream crossings, after recent heavy rains, added some unexpected adrenaline surges. Yes, those rocks are slippery when wet. Overall, it was a great hike, peppered with panoramic views of farmland and timber.

Rolling Meadows is very easy to walk (definitely more of a walk then a hike) and is relatively flat for the most part. Excellent views of the surrounding countryside although nothing dramatic like the overlooks in Shenandoah National Park. Trails are very well maintained and wide which is nice when I bring my dog. Several creek crossings as well. Hiked several times but can't beat this one a cool fall day.

Meadow part of trail is EASY. Climb to top of Lost Mountain is MODERATE. Scenery is wonderful, especially in meadows. Took hike on unseasonably hot day in early October with my dog. The meadow part of the hike is unshaded and was quite hot. I would recommend this trail for early- to mid-spring or mid- to late-fall for best outcome.

This is definitely not the easy trail! It’s the advanced trail! This trail is the yellow trail. In order to get to it, you have to hike a good portion of the easy blue trail (Rolling Meadows Trail). It definitely has a few places that are very picturesque but the yellow (Lost Mountain Loop Trail) is definitely challenging. 600 feet of elevation, up and down, little rocky, but nicely maintained and wide. Also, it is $5 for cars and they only take cash or check (good faith box).

hiking
11 months ago

This is NOT an easy trail, but it's rewarding. Lots of falling acorns and walnuts and plenty of horse manure to avoid when we were there mid-September. Beautiful views of The rolling hills of Paris, VA, which is my favorite place in northern VA.

hiking
11 months ago

Great Saturday morning hike with my dog. The front half of the trail loop is rolling meadows and the back half is up in the mountains with a creek running down the middle. I was the only person hiking with a few other guys mountain biking the front half. The trail is also open to horseback riding with pull thru parking for trailers. Parking is $5.

hiking
Tuesday, August 01, 2017

An easy afternoon hike with nice views! Great for the pup too!

Sunday, July 16, 2017

Combined Rolling Meadows with Washington's Ridge for a nice hike on a hot day. Rolling Meadows isn't much more than a walk but the two stream crossings are nice along with the views. Washington's Ridge adds a little challenge and some scenery.

hiking
Sunday, June 11, 2017

Nice views

hiking
Tuesday, May 03, 2016

More of a walk than a hike. Fields are nice but don't provide much excitement

hiking
Monday, January 04, 2016

This trail was much nicer than I expected. On a cold January day it was still scenic, so I MUST return this summer. I still need to do the rest of the trails in the park so if I have time, this one is worth repeating. There is some elevation gain, but not all at once, so you will hardly notice.

hiking
Tuesday, July 21, 2015

One of the most beautiful hikes I have ever been on. Beautiful views no matter where you are in the park!

hiking
Tuesday, July 02, 2013

One of my favorite hikes yet!! This was beautiful, with awesome views and creeks streaming by. I definitely recommend this hike.

hiking
4 months ago

hiking
5 months ago

hiking
11 months ago

hiking
Sunday, August 06, 2017

hiking
Sunday, July 23, 2017

trail running
Monday, June 19, 2017

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