The Old Sled Run at Oak and 1st Starts a November Walk With a Closing Date

In the 1950s, the slope at the corner of Oak and 1st Streets was a sledding run. It curved around the bend where stone stairs stand today, ran on toward what is now the Oak Lane Trail, and after dark it was lit by street lamps on poles. The Highlands Plateau Greenway still marks the spot with a gazebo, and the old track is now a 0.2-mile trail the Greenway rates as an easy walk.

For the eleven homes of Sanctuary on 1st, that corner is right next door. The developer's site plan places the enclave "between 1st Street and Oak Street on the west side of town," and it describes every lot as an easy five-minute walk to the middle of town. The trail behind the neighborhood is where Highlands' history begins to show. On the other end of a short walk, two indoor collections finish their 2026 seasons this month. For the first three weekends of November, you can walk the whole route from your door. After that, part of it closes until spring.

A Marsh, a Gazebo and Volunteer Labor

The sled run did not survive the decades unchanged. By the Greenway's account, the old course turned marshy, and it was converted into a trail in 2015–16. In July 2016, the Highlands Newspaper described the new trail as starting at the corner of 1st and Oak, following the old sled run, and ending "back near the Mill Creek Bridge."

The gazebo came out of the same push. In a January 2015 report, the Greenway listed continued work on the Sled Run Trail and the gazebo among its future projects. In March 2019, the Highlands Newspaper reported on a proposed Oak Street access connection to the gazebo. Greenway members Hillrie Quinn and John Akridge presented it, and most of the labor was expected to come from Greenway volunteers.

The corner at Sanctuary on 1st was built by volunteers, a few projects at a time, to bring back a piece of in-town winter history. The 2026 Chamber of Commerce feature "The Highlands You Haven't Met Yet" describes the restored path as running through an area that was once an informal gathering place for winter recreation.

From the Stone Stairs to Main Street

The sled run itself takes a few minutes. It is worth walking first because it sets up the rest of the route, which moves forward through Highlands' timeline.

1. The gazebo at Oak and 1st. This is the start of the Oak Street Sled Run Trail, at the neighborhood's corner.
2. The stone stairs. This is the bend the sledders rounded in the 1950s, and the trail follows the old course toward the Oak Lane Trail.
3. Into town. From the west side of town, the developer puts the middle of Highlands about five minutes away on foot.
4. 141 Main Street. This is Maria's House Museum, Highlands' newest cultural stop.
5. 524 N. 4th Street. This is the Highlands Historical Society's Historic Village, home to the oldest surviving house in town.

Maria's House Museum opened in May 2026, and admission is free. The collection belongs to Russ Chandler, who spent more than five decades gathering fine art, historical artifacts and military memorabilia. It includes 40 original Rembrandt etchings, many of them biblical scenes, Old Master paintings associated with the studio of Peter Paul Rubens, antique weapons and a suit of armor dating to 1540.

In its May 2026 issue, The Laurel Magazine traced the collection back to the mid-1970s, when Chandler began buying antique weapons at a New Orleans gallery. The magazine reported that he has been visiting Highlands since 1994 and quoted him as saying, "We love Highlands." The museum is named for Maria, with whom Chandler had talked about sharing the collection. According to the Chamber, some pieces were bought through Sotheby's and Christie's, and others turned up in antique shops and smaller markets.

The museum keeps weekend hours only: Friday and Saturday from 10 a.m. to 4 p.m., and Sunday from 1 to 4 p.m. Its published season runs May 1 through November 30.

The Oldest House in Town Closes First

The Historic Village on North Fourth Street holds an older layer of the town's story. The Elizabeth Wright Prince House was built in 1877 by millwright Arthur House, two years after Highlands was founded. It is recognized as the oldest surviving house in Highlands and is listed on the National Register of Historic Places. The same property has the Highlands Historical Museum and Archives, housed in a building put up in 1915 for the Hudson Library. It also has Bug Hill Cottage, a preserved open-air treatment structure from Dr. Mary E. Lapham's tuberculosis sanatorium, which opened in 1908.

This is the stop with the tighter deadline. The Highlands Historical Society's 2026 season runs May 1 to November 22. Hours are 10 a.m. to 4 p.m. Thursday through Saturday and 1 to 4 p.m. on Sunday. November 22 falls on a Sunday, so the village's last hours of the year are that afternoon. Maria's House stays in season for another week.

November, Weekend by Weekend

The two schedules only overlap on Friday, Saturday and Sunday, so the full route really comes down to weekends. Here is how November 2026 lays out from the Thursday this post publishes.

The weekend of November 20–22 is worth planning around. On Saturday, November 21, the Highlands Performing Arts Center has Mark O'Connor's An Appalachian Christmas at 7:30 p.m., so an afternoon in the museums can run straight into an evening show. Earlier in the month, the PAC lists Hotel California on November 7 at 7:30 p.m. and National Theatre Live's Golden Boy on November 12 at 5 p.m.

The Outdoor Half of the Route Keeps Going

The sled run is a Greenway trail, and the Greenway now runs about ten miles of connected trails through town. The outdoor gardens and trails at the Highlands Botanical Gardens are open all year. The Chamber's October feature points out that once the leaves drop in November, branches, trunks, rock, moss and rhododendron become easier to pick out.

The Greenway is also still growing near the Historic Village. The Highlander reported on October 29 that Greenway leaders have proposed an extension from North Fourth Street toward Little Bear Pen Road and Sherwood Forest Road. For access from the Pinecrest Road entrance, the Greenway asked the town to consider either a new 400-foot sidewalk on the right side of the road or a crosswalk from the existing sidewalk on the left.

For now, the gazebo at Oak and 1st is still the closest Greenway trailhead to the neighborhood, and the slope behind it is the same one people sledded down by lamplight seventy years ago.

At Michelle Michaud, we think a home's story includes the ground around it, like the sled run at the corner and the old houses a short walk away. If you own at Sanctuary on 1st and are starting to think about how to present your home, we would be glad to sit down and talk through the history and setting that come with it. Schedule a Complimentary Luxury Listing Consultation.