Big Summer Dirt Rides: Ditch the Car and Ride from Frederick



Long days are perfect for big meandering rides.  We like setting off in the afternoon and arriving back in town toward dark.  The setting sun is a bit cooler, the light is perfect for photographs, and there is usually less traffic.  We get lots of requests for more routes around Frederick.  There are 6 places to ride nearby, but we mainly stick to 3 of them:  Gambrill/Wolfsville and the Watershed, the Middletown Valley, and Sugarloaf.  These have minimal transport stages (boring suburbia) to get through and they all contain hills and dirt roads, our two main criteria for good rides.  The valley south of Thurmont is fine, but it’s higher traffic, has no dirt roads left, and no climbs to speak of.  There are some nice looking Covered Bridges though and plenty of farms.

All of the routes below start at Gravel & Grind. On Sundays there is free on street parking.  The shop address is 124 S. Carroll St, Frederick MD 21701.

Watershed Loop:

The Watershed is a swath of forest 12 miles northwest of downtown Frederick.  It’s laced with trout streams, lichen covered rocks, wandering families of bears and small ponds.  If you like hiking, fishing, climbing, dirt roads, mountain biking or swimming, it’s the place to go.  No maps, besides the Google map, so you just have to get out and explore.  It’s hemmed in by all sides with bigger roads or boundary markers, so it’s hard to get too turned around.  This ride takes you on all of the major dirt roads in the ‘Shed.  You’ll start with a 5 mile climb up Right Fork, passing a tumbling brook, a swamp, and a number of hidden but not far off-the-road ponds.  They’re hiding a 1/4 mile down fire roads, behind red or yellow forest access gates.  Reference a google map while riding to see if you are close to one, and check ‘em out.  They are all worth visiting!


On your way back down through the shed, you’ll do a stream crossing and another big climb. The descent back to the city is fast and bumpy and swoopy:  if you are not a seasoned descender, go slowly and take breaks.

Here’s a link to the route:

Don’t miss:

  • The Mountaindale Convenience Store on Mountaindale Road.  Ice cream sandwiches, cold water, coke in a bottle.
  • The rock formation at mile 14.4 on your left.  It’s across a small stream, last we checked there was a log bridge to get back there.
  • The fire road and pond on your left at mile 16.4.  The pond is a few hundred yards down a bumpy trail.  Walk it if you are unsure.


  • Plenty of water.  Only place to get more without a filter is the Mountaindale Store, and it’s pretty early in the ride.  I’d bring 3 bottles, at least.
  • Tools and a tube or two.  It’s rough and fast and dirt!
  • Lights that you can safely ride with after dark.  A 200 lumen headlight minimum



Sugarloaf Mountain Loop:

Sugarloaf Mountain is a privately held, publicly accessible mountain a few miles south of Frederick.  It’s surrounded by good dirt roads, and the mountain itself has a nice wandering climb to a summit with good views and places to eat lunch.  We particularly like eating at the weird old fort-like structure at the uppermost parking lot.

The ride heads south out of Frederick on a wide road.  Ride it on a Saturday or even better a Sunday morning or afternoon for the lowest traffic.  The transport stage is flat and fast, and a small group can knock it out quickly if they do some light pace lining.  The transport stage is prettier than most, once you clear the city you are in farm land.

As soon as you get off the main road, the riding becomes hilly, crossing the Monocacy River, passing by a Lily Pond farm, and climbing a steep paved section of Park Mills Road.  The climb is rewarded with a fantastic descent down Peters Road, one of the coolest dirt roads in the area.  It ambles along a small stream where heron are often seen fishing.

As you wind around the mountain, you’ll be on and off small dirt roads.  Sugarloaf Mountain road is long and straight and well covered by trees.  It empties into a small parking lot a the foot of the mountain.  There’s a water fountain in the parking lot.  Fill up and start the climb up the gated mountain access road to the over looks.  The first over look is on your right, but the main one is at the top of the climb.  Descending is fast and twisted, use caution.

The journey back to Frederick involves a bit of back tracking, but it’s well worth it.  You get to fly down Flint Hill and cruise next to a particularly scenic section of the Monocacy River.  You also pass thru tiny historic Buckeystown before returning to a transport stage and the city itself.


38 mile route here:

Sugarloaf has a longer than usual transport stage, but once you get there, the ride is worth it.

Don’t Miss:

  • Lilypons Water Gardens, if they are open.  Call ahead.  The grounds are worth a stroll.  On Lilypons Road.
  • Heron Watching on Peters Road, especially toward evening or early morning.
  • The fort at the top of Sugarloaf Mountain is a great place for lunch.  Or bring a light lock and hiking shoes and hike to the summit of the mountain.  It’s steep and filled with stone steps.  About an hour hike, with great rocks and views at the actual summit.

Things to know:

  • Ride this route in a small group for better visibility on the transport stage.  We’d also recommend using day time visible tail lights.
  • No stores along the route mean: bring water and food
  • Rough roads, bring tools and tubes


Middletown Valley: Dirt Roads and Steep Rollers

Middletown Valley is like the Thurmont Valley but arguably more scenic, hillier and it has dirt roads.  The dirt roads are just about as well manicured as dirt roads get, so this is a great ride to take a new dirt road rider out on.  You could ride this with 25mm tires, but we like fatter tires for more comfort, even on smooth roads.


Take a ride past downtown’s Baker Park before starting a few mile transport stage to get out of the ‘burbs.  You have to cross route 40, but you’d do it at a light, and it’s a long enough light to safely cross.  Once you take the left on Mt Phillip Road, it’s all country.  The big rollers start immediately, and they are tempered by even bigger extended climbs and some nice flat sections, especially down along Poffenburger and Richard Remsburg Road.  You’ll summit Teen Barnes Road for a great valley view and a screaming fast short descent.   Poffenburger and Bennies Hill Road both ride alongside a small creek, and there might be some secret swimming holes for the adventurous types.  You’ll cross two historic bridges and 4 gorgeous dirt roads before coming into Middletown, where you can snag Ice Cream Sandwiches before heading back.  The return route is dirt free but has some great wide open country roads and more rollers.  The Transport stage back to town is varied, so hopefully it feels less like a transport stage and more like a meander through town.

Route link here:

Don’t miss:

  • The old bridges on Bennies Hill and Poffenburger
  • The underground house on Harley Road
  • The view from the top of Teen Barnes Road
  • Ice Cream at the gas station in Middletown or Coffee at the Main Cup


  • All the usual ride stuff like tubes and tools.  There’s a water stop, so extra water isn’t a huge deal.