A Two Day Cycling Getaway on Maryland’s Eastern Shore

In place of a “normal” fall vacation week, my wife and I did two short outdoor getaways. First we drove to Staunton VA, stayed at a B&B, did some car touring while it rained, and hiked Crabtree Falls when the rain finally ended.

We came back home, did a few chores and then headed out to Maryland’s Eastern Shore. The weather really cooperated during this part of the plan – mid 60s and not a cloud in the sky.

Cross Island Trail, Kent Island MD

On the way to Cambridge MD, we stopped on Kent Island and did 20 miles on and around the fantastic Cross Island Trail.

Carole enjoying the sunshine at one of the viewpoints.
View from the trail out towards the Chester River

We ate lunch at the Big Owl Tiki Bar – you’d never drive there just for the food, but the location on the trail and the excellence of the view makes up for the mundaneness of the meal…

Killer View of masked cyclist and the Great Eastern Bay at Kent Narrows from the Big Owl Tiki Bar

From there we drove to Cambridge to burn some of my Hyatt miles at the Cambridge Hyatt and had an excellent dinner at Vintage 414 in downtown Cambridge.

Sunrise over the Choptank River view from our hotel room

After enjoying the view of the sun rising over the Choptank River, we headed out to fuel up for a planned 30 mile ride before we headed home. Coffee, an acai bowl and “Grandma’s banana bread” takeout from the Blackwater Bakery in downtown Cambridge was pretty tasty.

Blackwater Bakery in downtown Cambridge MD

The original plan was to do a 30 mile loop through and around the Blackwater Wildlife Refuge.

However, winds were 20 mph with gusts to 25+ which causes two problems: (1) Headwinds, of course, and Carole had done a lot more running than cycling this year; and (2) the rise in the water level of the Chesapeake Bay, combined with the sinking of the land level from development, means that some of the roads flood at high tide anytime there are high winds coming on shore.

So, we diverted to just doing 14 miles or so by circling the Wilderness Drive inside the refuge.

There are a few short side rides, one was a “pollinator refuge” along a path to an old graveyard.

One of a dozen or so gravesites showing dates from 1807 – 1860.

The short loop we did does take you past the Harriet Tubman Underground Railroad Visitor Center but it was closed because of Covid-19. The Blackwater Refuge visitor center is only open on weekends now.

So, we hopped back in the car and headed home, first doing the planned 30 mile loop by car. Sure enough, while Maple Dam Road was open to cars, there were many sections of flooded road – cycling through 6-12 inches of saltwater is never fun for me or for bicycle drivetrains…

We made a final stop on the way home for some fresh roasted coffee beans and a latte for Carole from Rise Up coffee in Easton.

Avid cyclist, sometimes touring cyclist. My main road bike is a Trek Domane SL6, my touring/unpaved riding bike is now a Jamis Renegade. I'm located in Maryland, about midway between Baltimore and Washington DC.

17 response to "A Two Day Cycling Getaway on Maryland’s Eastern Shore"

  1. By: BobinVT Posted: October 16, 2020

    Looks like a good adventure. The eastern shore seems really nice. My one experience there was a trip to Saint Michaels, where I spent a couple of days doing day rides out to Tilghman Island, Oxford, and a few other places. It was very cycle friendly and a great place to ride, but I do remember battling the wind every day.

    • By: jpescatore Posted: October 16, 2020

      Yes, we’ve done a lot of cycling in the St. Michael’s area – going down to Tilghman Island invariably has a stiff headwind one way or the other!

      The iconic ride is about a 30 mile loop where you start in Easton, bike to Oxford and take the ferry across the Tred Avon river then bike to St. Michaels, spend the day and bike back on roads.

      • By: BobinVT Posted: October 17, 2020

        I had actually hoped to do that loop, but unfortunately I was there in early spring, apparently about two days before the ferry started running for the season.

  2. By: NancyG Posted: October 16, 2020

    Nice trip, and I really like the sunrise shot over the Choptank. Smart choice to avoid those headwinds!

  3. By: gregblood Posted: October 16, 2020

    Good food or not, I want to go to the Big Owl Tiki Bar–not just for the ocean scenery and the Polynesian ambience, but for the hope of seeing a big owl there. Also, am I correct in assuming there are a lot of bees in the “Pollinator Refuge?”

    • By: jpescatore Posted: October 16, 2020

      There might be deep fried owl fritters on the menu – probably the closest you will get to an owl there!

      This time of year the Pollinator Refuge was pretty barren – all of the flowering plants that attract bees were pretty much dead stalks. Plus, if there is a bee within miles it will find my wife and freak her out – nothing!

  4. By: Bill Stone Posted: October 16, 2020

    Very nice! One of the features I like most about this group is getting close-ups of “exotic” bicycling locales like this.

  5. By: Lednar De Nalloh Posted: October 16, 2020

    First time I’ve heard of an acai bowl, sounds nice and healthy.

  6. By: Scooter Posted: October 16, 2020

    Looks beautiful. We really do need to make it back to the east coast some year. Great sunrise!

    • By: jpescatore Posted: October 17, 2020

      An acai bowl is kind of slushy made from acai berries, with bananas, strawberries, bluberries, chia seeds and sometimes granola on top – and usually drizzled with honey! I first tried one years ago at a coffee shop in Ocean Beach CA and recently they started showing up around here.

  7. By: Laura Posted: October 17, 2020

    Looks like a great getaway with perfect weather! Maryland has some great places to bicycle. Many years ago, before we began loaded touring, we did a Cycle Across Maryland week-long ride which included three days in the Delmarva and three days north of Baltimore. It’s the only time I did a century ride…figured I’d never have the opportunity on a more-flat route.

    • By: jpescatore Posted: October 17, 2020

      I did Cycle Across Maryland back in 1994 or 1996 or so – sounds like it may be the same one! We started in Cambridge, then had the century day from Federalsburg to Chestertown. The last 40 miles of that ride, from Dover to Chestertown was in killer heat and wind – people were dropping like flies The next day they put us on ferries to the Inner Harbor, very nice.

      An earlier CAM had stayed at the high school near our house in Ashton MD and we volunteered. CAM was a great ride but died out a few years later.

      • By: Laura Posted: October 20, 2020

        I don’t remember the year, but I do remember the century went to Dover, Delaware and it was only leaving there that the ride presented much of a challenge. I remember it being very hot and just before I finished, a girl overcome with heat was hauled off in an ambulance. I had at least three popsicles that day, trying to cool off. We met some folks there who we’d met on a Bike Virginia ride the summer before and had a great time. I also remember biking by Pickles Bar in Baltimore and there was one bad uphill that they made everyone get off and walk.

        • By: jpescatore Posted: October 20, 2020

          That was the same year! I didn’t do the Pickles Pub, after getting off the ferry I biked directly to the community college that was that night’s stop in Catonsville, which isn’t far from my home. My wife and young daughter (maybe it was 1994, she would have been 4) picked me up and I stayed at home that night. The next day it had rained overnight and we had a wet downhill and that climb they made us walk up for some reason.

          It was really hot that day, too. I had a room at the college that night – but it wasn’t air conditioned and had to be over 90 in the room. I went down to the pool and stayed until they kicked us out -probably got about 2 hours sleep that night.

  8. By: Rich-Illinois Posted: October 17, 2020

    Sounds like a great ride. The sunrise photo is excellent.
    Interesting about the land subsidence due to development.

    • By: jpescatore Posted: October 18, 2020

      There is a natural aspect to the land around the Chesapeake Bay settling – apparently the ice age caused ice sheets to push land south and it built up. That land has been settling ever since.

      But the rate accelerated in the last 20-30 years as development added structures and roads that increased the downward pressure, and the increased population pulled more water from the ground.

      It has been very noticeable the past 5 years of so all around the Bay – “nuisance” floods happen regularly when the winds blow on-shore and even a normal high tide hits.

  9. By: Rocky Posted: October 19, 2020

    Glad you got to getaway for awhile. Great photos! Love the masked cyclist!

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