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An old fashioned drive in the country

Plan about four and a half hours for this route, which is taken from the 2004 GWS summer Dine and Drive. This should give you the opportunity to enjoy both your Mercedes-Benz and a terrific drive along the west side of Maryland's Eastern Shore. The route is one BIG long loop, and getting lost is part of the fun. For our event we ended at The Robert Morris Inn in Oxford, where we had a wonderful dinner.

If you want to detour, go ahead, and feel free to stop at a roadside stand or a country store. There are plenty of places for a rest stop or a chance to pick up a snack a drink or local produce (in season) along the way.

As always, be careful to maintain the posted speed limits and watch out for Maryland wildlife. There are plenty of birds, turtles, deer and other animals that wander into your path along the way.

Starting Point

The drive starts at Kent Narrows & the Chesapeake Exploration Center

  • Turn RIGHT out of the parking lot and follow the road to the STOP
  • Turn LEFT and go under Rt. 50 to the stop
  • Turn LEFT onto Rt. 18/Main Street and go over the draw bridge. If it's up, turn off your engine, get out and enjoy the scenery – this is the way it used to be before the "highway" was built
  • Follow Rt. 18 – Main Street through Grasonville until the road merges onto Rt. 50
  • At Rt. 50, bear to the RIGHT and merge into traffic
  • Turn RIGHT onto Rt. 662, just before Chesapeake College

First Stop: Wye Mills/Wye Oak/Wye Church

  • Take Rt. 662 to Wye Mills/Wye Oak/Wye Church
  • Stop at the Wye Oak (now gone) was the middle of the three trees. Stop and take a moment to walk around back down to the Mill – or up to the church
  • Continue South on 662 until it meets up with the Ocean Gateway again Rt. 50
  • Turn RIGHT onto Rt. 50
  • Continue on Rt. 50 to Rt. 322 the Easton Parkway
  • Bear RIGHT onto Rt. 322 and follow until it picks up Rt. 50 again
  • Continue on Rt. 50 towards Cambridge watch out for the Speed Awareness Zone
  • Cross the Choptank River Bridge and stay in the right hand lane
  • At the end of the bridge make a RIGHT onto Bryn Street, then turn RIGHT on Rose Hill Place
  • Turn RIGHT into the Sailwinds Visitor's Center

Second Stop: The Sailwinds Visitor's Center in Cambridge Maryland

Stop, Park and visit the Visitor's Center, a great place to view the Choptank River while taking a break and learning about the area.

  • LEFT out of the Parking lot onto Rose Hill Place
  • LEFT onto Bryn Street and RIGHT onto Rt. 50 (Be careful of traffic)
  • Stay in right hand lane and make the NEXT RIGHT onto Maryland Avenue

The Cook's Tour of Cambridge

An opportunity to drive slow and see the town!

  • Go West on MARYLAND AVE. MARYLAND AVE crosses Bridge and becomes MARKET ST.
  • Bear RIGHT after crossing Cambridge Creek Bridge
  • Turn RIGHT onto GAY ST.
  • Turn LEFT onto Court Lane
  • Turn RIGHT onto High Street
  • Follow High Street to the right around the circle to the LEFT at Long Wharf
  • Turn RIGHT onto Water Street. Water Street becomes Hambrooks Blvd. Hambrooks becomes Bellevue Follow along river
  • Turn RIGHT at Oak Street Stop sign - the road becomes Riverside, then BayView
  • Turn RIGHT on Hambrooks
  • Turn LEFT on Glasgow (heads back into town)
  • Turn LEFT at High Street stop light
  • Make an immediate RIGHT on Poplar. Poplar becomes Race Street

Dorchester County – The Country Side & The Blackwater Refuge

If you drive enthusiastically, be careful of the curves and conditions in the road.

  • At Stop light is Route 16 (Church Creek Road). Continue straight ahead onto Maple Dam Road
  • Follow Maple Dam Road through the Blackwater Refuge and it turns into Robbins Road
  • If it has recently rained, continue straight and skip the next two instructions
  • If it hasn't rained recently, turn RIGHT onto Liners Road. The road is paved, but has some overwash of sand, so drive carefully
  • Turn LEFT onto Blackwater/Liners Road
  • Turn RIGHT onto Golden Hill Road, Rt. 336
  • At intersection with 335 continue straight onto Rt. 335

Chesapeake Water views – you asked for it

  • Follow Rt. 355 Hooper's Island Road Till the very very END. There are a couple of unmarked turns - stick with what feels like the road (usually going to the right works)!
  • On Hooper's Island is a restaurant called Old Salty's – very good food
  • At the VERY VERY END is a very small cul-de-sac – turn around and head back up Rt. 335
  • At the intersection of Rt. 335 & 336 make a LEFT and stay on 335
  • At Church Creek turn RIGHT onto Rt. 16 Follow until Rt. 50
  • At Rt. 50, Cambridge turn LEFT onto Rt. 50

The Final leg of the drive

  • Cross over the Choptank River Bridge – Sailwinds Visitor Center will be on your left now
  • Take Rt. 50 into the town of Trappe move into the left hand lane
  • Make a LEFT at the light onto White Marsh Road/Old Trappe Road and go into the town of Trappe
  • Continue Straight on White Marsh Road until it stops at Almshouse Road
  • Turn LEFT onto Almshouse Road and follow until Rt. 333
  • At Rt. 333 Turn LEFT
  • Follow Rt. 333 until Oxford, and SLOW DOWN, because Oxford's 25 mph speed limit is strictly enforced
  • At the other end of town – just before the Oxford Bellevue Ferry is the Robert Morris Inn on your right

If you'd like to sample the food at the Robert Morris Inn, enter the parking lot.

The return trip

  • Follow Rt. 333 East until you get to Rt. 322

We Hope you enjoyed this opportunity to drive and see the sights of this very interesting part of Maryland.

Thank you joining the Greater Washington Section of the Mercedes-Benz Club of America, Inc. and for your participation in this event.