Peddling the ’58 (and Beyond!)

By Adam Pettengell, in Governors

This is the big one! No, it’s not the famous yo-yo move, but instead the big loop incorporating Gordon’s Pond Trail and the Junction & Breakwater Trail! There is NO better route to take in all the beauty surrounding us at the beach. The biggest problem you’ll encounter is, do you stop every time you see an amazing view to take a photo? Tough decisions right?! Ha. You can experience just under 16 miles of the best scenery around, and I promise there are numerous stops to hydrate, if you get what I mean.
Here is the scenario. You went out last night to Striper Bites and had an amazing meal and drinks. Oh, it’s great to live close to so many amazing restaurants! You woke up in your new home at Governors and feel the need to work off all the goodies you ate. It’s all about balance. You plant the idea of a gentle late morning bike ride, including lunch of course. And just like that you’re out the door and seeking the trail!
Jump on your bike, leave the community and turn right on the Junction & Breakwater Trail. Travel along the trail parallel to Gills Neck Road. Then, cross the road at the crossing just after the Hawkseye community. Continue on the trail and pedal parallel to Breakwater, then bear right and draw parallel to Freeman Highway (US 9). You will briefly join Freeman Highway and venture over the bridge, but keep cycling straight and then bear right onto Cape Henlopen Drive. If needed, stop number one is On the Rocks bar by the Cape May-Lewes Ferry. You can then enter Cape Henlopen State Park and get on the bike trail. This will take you by one of the watch towers which has an incline (pretty rare to find an incline amongst all of this flat land). You then wind down and go behind the camping area. The bike trail will connect to the walking dunes trail, which brings you to Dune Road in the park. You can take the trail alongside Dunes Road all the way to the Herring Point car park. This will lead you to Gordon’s Pond Trail. You can follow this trail from Lewes to Rehoboth. You’ll go past the watch towers, the Overlook (great spot for pictures) and then in the blink of an eye, you are in Rehoboth and leaving the park.
You then connect onto Ocean Drive! Not a bad road name, right? In fact, isn’t that a song? Anyway, when you come to the junction you can either take Columbia Avenue all the way up to Grove Park in Rehoboth, or Henlopen Avenue. I actually think Henlopen Avenue is best. This allows you to take the small trail around Grove Park and come out behind the Rehoboth museum.  From there, go over the bridge on Rehoboth Avenue, turn right on Church Street, and left on Canal Crossing Road. The second stop is available here to visit our friends at Revelation Brewing! It would be rude not to in my opinion, and that Cocoa-nut Joe Porter is just pure bliss. At the end of Canal Crossing Road, you have two options on Hebron Road to join up to the Breakwater Trail. Left or right you will end up on the trail, but it’s probably quicker to get off the road by turning left. You then follow the Junction and Breakwater Trail back from Rehoboth to Lewes and exit the trail into the Hawkseye community. Continue through the middle of the median on Golden Eagle Road and then follow the trail into the Senators community. You’ll come out parallel to Gills Neck Road, and home is in sight! Of course you could go past Governors, jump across the lights and pop into Big Oyster or Mr. P’s for lunch and a beer. Hey, you deserve it. You just did a little under 16 miles!
You finish that route and tell me it wasn’t amazing and I’ll…eat my socks! Never in doubt and you will want to go again and again, and not just because of the stops you can make along the way.

Route map for Governors The Lewes And Rehoboth Loop by Adam Pettengell on

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