Since 7 a.m. on Monday, August 3, Vineyard Avenue has been closed between Chapel Hill Road and Grotto Lane. NYSDOT expects it to stay closed through November, weather permitting. On the state map this is U.S. Route 44/State Route 55. In Highland it is simply the main road toward New Paltz, and the reason it is closed is a creek most drivers cross without seeing.
That creek is the Twaalfskill. It is also the subject of the Town Historian's talk at Highland Public Library on October 13. Two days earlier, on the hamlet's other old corridor, the Hudson Valley Rail Trail, its caboose turns 100. Much of Highland's fall calendar comes back to the same few pieces of old infrastructure, and the creek is the one causing the detour.
Culvert C870030, and why the whole road closed
The Town of Lloyd's Highway Department notice gives the project's working name. NYSDOT is replacing culvert C870030, which carries Route 55/Route 44 over the Twaalfskill Creek, and the work zone covers about 1,056 feet between Chapel Hill Road and Grotto Lane.
The road can't stay half open with flaggers alternating lanes because the work needs a full closure. The Town's notice says vehicles cannot cross the work area at any point during the replacement. People on foot have one option. An on-site accessible shuttle drives pedestrians around the work zone, with signs pointing to the service.
The end date depends on whose notice you read. The Town described the closure as lasting about three months from August 3. NYSDOT's release says "through November." The most recent dated public update we found ran in the Southern Ulster Times on August 5. It repeated the through-November, weather-permitting timeline and sent drivers to the posted detour. Neither agency has published the detour's turns, so the signs on the road are the guide. NYSDOT points travelers to 511NY for current conditions.
A culvert sounds like a minor fix. For the next couple of months it decides how a large part of the hamlet gets west.
What the Twaalfskill used to run
Highland's Town Historian, Joan Kelley, is giving a talk with a title that reads like a summary of the creek's past: "Factories Before Electricity: Mills along the Twaalfskill." It runs October 13 from 6:30 to 7:30 p.m. in the Meeting Room at Highland Public Library, 14 Elting Place.
A historical marker for the Deyo Steam Mill gives a sense of how crowded that industrial era was. Brothers Aaron and John C. Deyo built the mill between 1859 and 1860. It was the area's first mill to run on steam instead of water wheels, and it made sashes, blinds, doors, moldings, wheelbarrows, stair rails, and furniture. The brothers dissolved their partnership in 1865, and Aaron ran the mill until he sold it in 1868. By 1875, maps labeled it the W. Deyo Sash and Blind Factory, one of four active mills at New Paltz Landing. The marker describes its neighbors as grist, cider, and plaster mills but does not name them.
The Deyo story stands out because the mill was the exception. It ran on steam at a time when the mills around it ran on water wheels. By 1887 Aaron Deyo had started a separate carriage-bow factory in Highland, and according to the marker, the old mill building is a residence and artist's studio as of 2026.
The marker covers the neighboring mills only by type. Kelley's talk is the place to hear which mills stood along the creek and where.
Where the creek is still visible
Most of the Twaalfskill's route is easy to miss from a car. Two local walking pieces from AboutTown trace it. One is a Highland history walk published in Summer 2011, and the other is a creek profile from Summer 2019. Both predate this year's construction, so trail conditions and access may have changed. Here is the route they describe, from the river side moving inland:
- The footbridge near the river. A Scout-built footbridge crosses the creek and links Bob Shepherd Highland Landing with Johnson-Iorio-DiLorenzo Park at the abutment of the Franklin D. Roosevelt bridge. The 2019 piece describes it as part of a route connecting the upper Walkway path, Highland Landing, and trail connections toward Franny Reese Preserve from Oaks Road.
- Under Route 9W toward Tillson Avenue. The 2011 walk leaves the Walkway, passes under Route 9W, and comes out west of the underpass heading toward Tillson Avenue. At the bottom of Tillson the creek runs past the Inn at Twaalfskill.
- The replica wheel on Vineyard Avenue. The same guide points to a replica mill wheel in the creek at Vineyard Avenue, next to a former mill site that later housed Pratt's Lumber.
- Mile Hill Road. The 2019 piece describes the creek coming down along Mile Hill Road and passing under it at the fork with Ransom Road, with strong flow at the crossing during the spring thaw.
The replica wheel stands next to the former mill site on the same road that is now closed for work on the creek. Highland's water-powered past and this fall's detour sit within a short distance of each other on Vineyard Avenue.
Sunday on the hamlet's other old corridor
The Hudson Valley Rail Trail Association is holding two programs on the trail on Sunday, October 11, from 1 to 3 p.m. The Rail Trail Association's event page calls it "two events," and you can attend one or both.
- New murals. Artist Jennifer Keltos will be on the trail at the second underpass west of the Tony Williams Town Park parking lot on South Riverside Road. She will talk about the new murals there and the local history behind them.
- A 100-year-old caboose. The trail caboose at 75 Haviland Road turns 100, and the Association is offering tours along with an introduction to the region's railroading past.
The event page shows a stray "Sep 30" in its time field, but the event description and the Town of Lloyd's notice both give October 11.
The caboose has had work done this year. At the Association's annual meeting in June, the Southern Ulster Times reported that exterior repairs and painting on the Haviland Road caboose had begun. The same report listed pavilion, landscaping, and restroom improvements already completed. The next project is the Ford Farm Bridge. Plans call for structural repairs, new decking, safer railings, and a 150- to 200-foot unpaved loop connecting the bridge to the paved trail. That bridge work was described as moving ahead in June. It is not part of the October 11 program.
The creek and the rail line are separate stories with the same pattern. Each involves old infrastructure that someone is still maintaining in 2026. The state is doing it with a new culvert, and a volunteer association is doing it with paint and new decking.
The dates, in order
These are the dates through mid-month, plus the two things running in the background all season.
- Saturday, October 10, 10 a.m. to 1 p.m. The Fourth Annual Family Scarecrow Building Event, rescheduled to this date, takes place rain or shine at the Lewis DiStasi Jr. Pavilion, 39 Main Street.
- Sunday, October 11, 1 to 3 p.m. Mural unveiling with Jennifer Keltos west of Tony Williams Town Park, and the caboose centennial at 75 Haviland Road.
- Tuesday, October 13, 6:30 to 7:30 p.m. Joan Kelley on the mills of the Twaalfskill at Highland Public Library.
- Daily, 10 a.m. to 5 p.m., through mid-November. DuBois Farms at 209 Perkinsville Road keeps its seasonal hours.
- Through November, weather permitting. Vineyard Avenue stays closed between Chapel Hill Road and Grotto Lane. Follow the signed detour. Pedestrians can use the shuttle.
The scarecrow event on Main Street, the caboose tour on Haviland Road, and the library talk on Elting Place fall on three days in a row. The same small creek connects the talk to the detour signs that will stay up after all three events are over.
If you'd like to talk through what this season's road work and the hamlet's history mean for a home in Highland, Isabel R. Alves is happy to listen and share what she knows about the Town of Lloyd. Let's Connect.
