Electric Bike cyclists can do a bit more than most all-manual peddlers. We came up with rides tailored to e-bikes that are away from busy bike trails.

Free up your assist button and let the bike roll.

Monkton Ride

Guided tour

$89 per person for 2-4 hour rides

14- 30 miles | VERY hilly

START: Pedego, 1901 Monkton Road, Monkton, MD — (E-bike rentals available)

Pedego Electric Bikes of Baltimore County noticed e-bike owners looking for adventure and put together a couple of rides through the Monkton, Maryland, countryside.

Pedego guided tours take you past horse estates and historic colonial county manors. Stops can include Inverness Brewery, Ladew Gardens or Royal Rabbit Vineyard.

The ride is 14 miles when it begins, but can be extended to up to 30 miles if riders get comfortable on e-bikes and want to spend a little more time in the country.

This is a VERY hilly area. Regular bikes are not recommended even if the rider is in shape and experienced on hills. Owner John Lebo points out that manual cyclists simply can’t keep up with e-bike riders, who have to kick up the assist on hills to maintain balance.

These are roads without shoulders for the most part, so it’s safest to ride with a group.

Monkton Pedego also offers a scenic Southern Pennsylvania tour through the rural countryside on dirt and gravel roads, through woods, past streams, and family farms.

The route on the map above shows the general area that Pedigo uses. The actual route will change depending on the weekend. Below is a Ride With GPS map of a similar route that shows the elevation.

Herrington Bay Ride

Go On Your Own

21 miles | Very hilly

START: North Beach Public Lot, 9125 Chesapeake Ave, North Beach, MD

This is also a hilly ride through the countryside, Maryland’s Western Shore. You’ll ride past the Chesapeake Bay at several points and up around horse-country hills with estates overlooking the Chesapeake tributaries.

It starts in North Beach, famous for the large public beach on the Chesapeake Bay. The route follows the shoreline until you get to the Trotts Branch river. It doesn’t have a bridge there, so you have to go up into the hills around the Chesapeake Bay tributary.

On your way into Deale, Maryland, you’ll go past Herrington Harbour North, a massive marina. Stop by its historic village, a collection of small buildings saved from destruction by the marina owner and set up by the local historical society as a hands-on museum.

Deale is a modern fishing village centered around fishing charters and sailing into the Bay. It is not especially historic like other Chesapeake Bay towns, but it does have several seafood restaurants featuring Chesapeake Bay fish, oysters, and blue crabs.

The way back takes you into the countryside, but let that assist help and enjoy those hills. The route winds you back to the shore roads and into North Beach.

Just south of North Beach is Chesapeake Beach. No public beach there, but it does have crab houses. Several have gaming in a back room, due to a deal with the state legislature years ago.

Many of the roads on this route do not have shoulders, so you’ll have to ride with traffic. Make sure you have lights on the bike and reflective clothing. It’s a popular route for regular cyclists, so you’ll have to deal with them too.

Blackwater Wildlife Refuge

Go On Your Own; Guided tours available for other routes

Hoopers Island Loop: 53 miles / Bishops Head Loop: 49 miles | FLAT

START: Harriet Tubman Museum Visitors Center, 4030 Gold Hill Road, Church Creek, MD Or Blackwater National Wildlife Refuge Visitor Center, Key Wallace Drive, Cambridge, MD

This part of the Eastern Shore is flat. Very flat. However, you’ll enjoy those e-bikes in the wind that sweeps across the vast Blackwater National Wildlife Refuge, one of the largest tidal wetlands on the East Coast.

Those winds make long rides tough for manual cyclists. Turn up the assist and enjoy this beautiful ride.

Hoopers Island Loop

This 53-mile route takes you to Hoopers Island, which is somewhat like Smith and Tangier Islands. Not so isolated, but locals do have a different way of living life.

Hoopers is a chain of three islands. The first two islands are connected by a causeway. The third is reachable only by boat.

If you’re tight on time, at least do a quick spin around the first island. It also has Old Salty’s, featuring home cooking in a former high school. The crab cakes are amazing. It’s the island’s only restaurant.

On the way back, you’ll go through low marshes. In high tides and after recent rains, the road in this part tends to flood. Be aware that you might have to ride through some water. A causeway takes you through a series of tidal ponds.

The Ride With GPS Route below is similar to the Google Maps route above and shows elevation.

Bishops Head Loop

This 50-mile route goes down a peninsula into the Hooper Strait Sanctuary to Bishops Head, Maryland. There’s not much there, but it’s a beautiful, ghostly ride.

The map takes you to the Karen Noonan Center on Tide Island, 20 acres of marsh in southern Dorchester County. The access road is occasionally underwater during high tide.

The education center is part of the Chesapeake Bay Foundation.

Bike Rentals and Guided Routes

Blackwater Adventures has bike rentals and offers tours through the wildlife refuge. The shop is open during the normal cycling season. Call ahead to see if have e-bikes. They do rent manual bikes.

The tours depart 9am & 1pm, going through the scenic refuge with a stop at the Blackwater National Wildlife Refuge visitors center, Layton’s Chance Winery, or deep into the wilderness along Marsh Road.

Here’s the traditional Blackwater Wildlife Refuge bike route.

A bit longer version.

Chestertown -> Eastern Neck Refuge or Betterton

Go On Your Own

65 miles | Mostly flat, but some hills

START: Wilmer Park, 230 S. Water Street, Chestertown, Maryland

This 65-mile loop can easily be shortened by going from historic Chestertown to either Eastern Neck Wildlife Refuge through Rock Hall or to Betterton. The Betterton end will be hilly. The Eastern Neck end will have some hills.

You’ll be riding on highways either way, but the main roads have shoulders. The county highways won’t have shoulders. Use your bike lights and reflective gear.

Rock Hall/Eastern Neck Portion

You’ll spend much of this ride going through farmland. The highways have nice shoulders for the most part until you get to Rock Hall.

Rock Hall is a small Chesapeake Bay town surrounded by marshland. It has a grocery store and restaurants so you can stock up on provisions or have lunch.

The road from Rock Hall to Eastern Neck Wildlife Refuge doesn’t have a shoulder, but it’s not usually heavily traveled.

Eastern Neck is actually on an island. It offers wonderful views of the Chester River where it enters the Chesapeake Bay.

Betterton Portion

This is a ride through vast Maryland farmland. Because of that, the roads have wide shoulders most of the way (for ag equipment).

It’s hilly and challenging. You’ll have to peddle around Chesapeake Bay tributaries, which means up hills and down again. On the bright side, these hills are much shorter than Monkton and other sections of the Western Shore.

You’ll turn around at Betterton, a former Victorian beach resort. The only remaining part of that era is the big beach below the town. The hill overlooks the northern end of the Chesapeake Bay.

The beach has full facilities so you can have a quick swim and rinse off before heading back.

Easton -> Trappe & Oxford or Tunis Mills & Bellevue

Go On Your Own

61 Miles | Some hills at the start and end of the route

START: Idlewild Park, 115 Idlewild Ave, Easton, Maryland

This fun loop takes you through Eastern Shore horse country down narrow, tree-covered lanes similar to those in Kentucky horse country, through tiny Tunis Mills then, along with prime Eastern Shore views around the Tred Avon River on the way to historic, white-picket fence-lined Oxford, Maryland.

You can do the loop only during the normal cycling season. The historic Oxford-Bellevue Ferry is closed during the winter. Check the ferry website for the ferry times and fees.


If you’re riding off-season, the north side of the loop takes you through Tunis Mills and ends you at Bellevue, a park that looks across the Tred Avon River toward Oxford, while the southern side loops Jamaica Point and goes into Oxford.


North Loop Section

The northern end of the loop goes through Maryland’s Eastern Shore horse county, around several Chesapeake Bay tributaries, and through Tunis Mills, a small scenic town.

You’ll ride down county tree-covered lanes with no shoulders. Many sections go through marshy-pine forests so the lane is humped up above the forest bottom.

These lanes are wonderful on hot summer days.

The busy roads have shoulders. Some have wider shoulders than others, but it helps.

South Loop Section

The southern end of the loop goes into Eastern Shore farmland. This is where you’ll hit a few hills. They’re not big hills, but when you’re riding flats, it’s a bit of a peddle. This is where you get to enjoy the e-bike assist.

Either way, you take, you’ll go through historic Oxford. Always worth a visit in the summer. You’ll find a gorgeous tree-shaded town park overlooking the Tred Avon River.

The business area is all of one block, but it has a country store, the Oxford Market, that makes sandwiches and sells adult beverages. The main street is lined with historic homes behind white-picket fences. The colonial Robert Morris Inn, the oldest full-service inn in the U.S., is down by the waterfront.

If you have to wait for the ferry, swing by the Scottish Highland Creamery by the Oxford shipyard.

This route was designed by the Chesapeake Cycling Club. Thank you ‘C3’!

If you want to ride this area with a group, the Chesapeake Cycling Club hosts the Tri-County Classic with two routes, a half metric century (33 miles) and a full metric century (66 miles) in May. This is a registered ride with an entry fee, but you get free stuff for the ride, rest stops with food and water, and a finish-line party.

St. Michaels -> Tilghman Island & Neavitt Landing

Go On Your Own

48 Miles | Flat

START: St. Michaels Nature Trail Park, 908 S. Talbot St., St. Michaels, Maryland

Tilghman Island painting on side of building

This route is a favorite. It’s always fun to visit St. Michaels, and Tilghman Island is peaceful with wonderful water views as well as interesting. If you tack on Neavitt Landing with its amazing expansive vista of the Cook Point Sanctuary, well then, you have a great ride.

It’s a challenging ride for road bikers because of the wind sweeping across the peninsulas, and the rough asphalt repaving between Bozman and Neavitt. E-bikers should enjoy it.

We start the ride along St. Michaels nature trail. It’s busy with walkers, so you need to keep the speed down, but it’s a scenic ride behind St. Michaels’ busy downtown.

Tilghman Island

Tilghman Island

It’s smooth asphalt roads with wide shoulders between St. Michaels and Tilghman Island, along farmland with the Chesapeake Bay on the other side. It turns to evergreen woods and marshland close to the island.

Once on Tilghman Island, the shoulders go away and you’re riding on smooth, crusty rock-and-oil roads to the tip of the island.

Tilghman has several places to stop for lunch. Be sure to swing by Dogwood Harbor to check out the waterman boats.

Then, back you go the way you came.

Neavitt Landing

Cycling to Neavitt Landing

Keep an eye out for the Bozman/Neavitt turn off of St. Michaels Road on the way back. This adds nearly 16 miles to the trip, but the view from Neavitt Landing is worth it.

You go through Bozman on the way, a tiny town with a church and several homes. Neavitt is only slightly bigger with a church, park, and private homes. There are no stores or restaurants along this stretch, so make sure you’re stocked up on water and nutrition.

Keep going past Neavitt, a little less than a mile, to find Neavitt Landing.

The return is back down the road, with a right onto St. Michaels Road to return to St. Michaels.

The two Ride With GPS Routes below separate Tilghman Island and Neavitt into separate routes.

Digiprove sealCopyright secured by Digiprove © 2022