Through November 30, driving into Cape Henlopen State Park to ride the bike loop costs $10 for a Delaware-registered car. On December 1 it costs nothing. At the same time, crews are lined up to add a new trail segment inside the park, and DelDOT is finishing the last phase of the Georgetown-to-Lewes Trail. So the cheapest months to use the trails around Lewes are also the months when their gaps are being closed.
That makes winter worth paying attention to. The network you ride in January is the version that is about to change.
December 1 removes the price of a Cape Henlopen ride
Delaware State Parks charges a daily entrance fee from March 1 to November 30. At ocean parks like Cape Henlopen, it runs $10 per day for Delaware-registered vehicles and $20 per day for out-of-state vehicles, according to the state parks fee schedule. Outside that window, no daily fee is charged. A weekly loop ride that would cost $40 a month in fee season costs nothing from December through February.
Inside the gate, two routes make up most trail mileage. Delaware Greenways lists the Gordons Pond Trail at 5.2 miles, with a northern access at the Herring Point parking area and a southern access at the Gordons Pond parking area. It puts the park's paved bike loop at 3.3 miles.
If you don't own a bike, the park has a free loaner program. The Friends of Cape Henlopen Bike Barn usually lends bikes Wednesday through Sunday, 10 a.m. to 3 p.m., weather permitting. The last bikes go out at 2 p.m. and are due back by 2:45 p.m. The group says winter cold can close the barn early and suggests calling the Seaside Nature Center to check before you go.
The bike loop is getting a new segment along Post Road
Free entry makes the loop easier to visit. Construction this season will also make it easier to get around once you're inside. The Cape Gazette reported on November 6 that the park had awarded a $1.25 million contract for a trail along Post Road. It will run north beside the road from the first entrance to the main bathhouse parking lot up to The Point's comfort station parking lot.
Matt Ritter, director of DNREC's Division of Parks and Recreation, told the paper the contractor was waiting on materials and work was expected to start shortly. The aim was to finish by the end of the year if everything goes as planned. Statewide trails funding and the federal Recreational Trail Program are paying for it.
This segment matters because of where it ends. The Point has the park's most seasonal access rules. Its oceanside beach reopened September 1 this year, and the bayside beach stayed closed until October 1 for migrating shorebirds, the Cape Gazette reported in August. Once finished, the new trail will connect the main bathhouse lot to that end of the park.
A second project is further off. Where the Junction and Breakwater Trail meets the park entrance, trail users now ride on the road shoulder in front of SPI Pharma. A DNREC end-of-season report describes plans to work with the company to move its perimeter fence and build a trail segment off the roadway. Ritter called it a long-range project and said no funding is available for it right now.
The Georgetown-to-Lewes Trail is finishing its final phase
The longest change is happening inland. The Georgetown-to-Lewes Trail is planned at 17 miles. Its final stretch runs from Fisher Road near Milton to Airport Road in Georgetown, according to the Cape Gazette. DelDOT's 2026 bicycle program update says construction on that phase began in September 2025 and is expected to be complete by spring 2027. The work covers a multi-use trail along the state-owned rail line and intersection improvements where the rail line crosses roads.
Part of that new section already hosted a race. On October 17, DelDOT ran the Georgetown-to-Lewes Trail 5K between Gravel Hill Road and Park Avenue, held in honor of Bill Conway and benefiting the Delaware Aerospace Education Foundation. DelDOT's Charles McLeod told the Cape Gazette that the rest of the final segment would not be ready by race day, so the official public opening would come later.
For Lewes riders this winter, the Lewes end is the usable end. Delaware Greenways counts 11 miles of the trail in use, starting at Gills Neck Road and passing Monroe Avenue, the Lewes Library, Kings Highway and Savannah Road on its way north. When the Georgetown phase opens, the same ride from town will go all the way to Airport Road.
There is also early work on a Milton branch. In September, DelDOT surveyed the public about a Milton connection starting from Hudson Park off Route 9. The proposed route is five to seven miles, the exact path is still undecided, and the study was expected to take about a year, the Cape Gazette reported.
Where to start a winter ride from town
All of these routes meet at a few access points in and around Lewes. Delaware Greenways lists these, and each one suits a different kind of outing:
- Monroe Avenue trailhead by the Lewes Library. It has ample parking, restrooms, an information kiosk, a water-bottle filling station, a fountain and a bike-repair station, with a second kiosk and rest area across Savannah Road.
- Gills Neck Road. This is where the Junction and Breakwater and Georgetown-to-Lewes trails start, with bike parking at Gills Neck and Savannah Road, about a quarter mile from the library trailhead.
- Wolfe Neck Road trailhead. Parking, restrooms and a water fountain partway along the Junction and Breakwater.
- Cape Henlopen High School and behind Tanger Outlets off Holland Glade Road. Two more Junction and Breakwater parking options toward the Rehoboth side.
The Junction and Breakwater itself is 5.8 miles. With connecting segments, the ride from Gills Neck Road to Rehoboth comes to about 7 miles.
Two Lewes bike shops sit right beside these access points. SeaGreen Bicycle is at 209 Monroe Ave., across from the Lewes Public Library on the Junction and Breakwater Trail, and it rents bikes. Lewes Cycle Sports rents bikes from its Savannah Road shop near the same trail. It also delivers rental bikes to the Lewes ferry terminal year-round, which helps when visiting family come over on the ferry. Shop hours change with the season, so call ahead before a winter rental.
For coffee before or after a ride, the Lewes Chamber of Commerce directory lists Notting Hill Coffee Roastery & Lewes Bake Shoppe at 124 Second Street. That's in the downtown district, a short ride from the Gills Neck Road trail end.
Group outings between now and New Year's Day
If you'd rather ride or walk with a group, a few organized outings are on the calendar this winter. All of them use the trails covered above.
- Friday, November 20. Sussex Cyclists hosts a brewery gravel and trail ride from Lewes Brewery Company, listed at 21 miles and 13 mph.
- Friday, December 18. The same 21-mile, 13-mph brewery ride runs again from Lewes Brewery Company. Details are on the Sussex Cyclists calendar.
- Friday, January 1, 2027. Cape Henlopen State Park hosts a free First Day Hike called History in the Pinelands, starting at 9:30 a.m. Meet at the Pinelands Trail and Fort Miles trailhead in the lot across from the Observation Tower. It falls during the no-fee months, so the hike and the drive in are both free.
By the time daily entry fees return on March 1, the Post Road segment may be open, and DelDOT's spring 2027 target for the Georgetown phase will be close.
If being able to ride to a trail from your own front door is on your list for a next home in Lewes or elsewhere in Sussex County, Tim Arnett and Patriot Properties Group can help you figure out which neighborhoods connect to which trailheads before you start touring homes. Let's Connect.
