Majestic Transportation Services & Limo Inc.
Route 211 gives the area a rather ordinary first impression. The strip has shops, chain stores, and enough traffic lights to test your patience. It’s not exactly the sort of place that makes you pull over and start exploring.
But judging an entire city by its busiest highway is a bit like judging a restaurant by its parking lot. If you’re wondering what to do in Middletown, NY, beyond the usual sights, you’ll find some interesting corners that require a little wandering.
The Paramount Theatre at 17 South Street opened on June 12, 1930. A parade, a giant electric sign and a screening of The Big Pond, starring Maurice Chevalier, marked the occasion. Back then, they cooled the audience by blowing air over enormous blocks of ice. It worked, although the room turned humid.
Air conditioning finally arrived in the late 1950s, but it came at a cost. The original Wurlitzer organ had to make way for the modern equipment. Another Wurlitzer, installed in a New Jersey theater in 1923, now sits in the auditorium, where volunteers still maintain it.
The building closed in 1978. The Arts Council of Orange County restored it and reopened it in 1985. Today, the city runs it with movies, live performances, and a classic film series on select Saturdays in spring and fall. Check the event calendar first, since the lineup changes.
Just down the street from the Paramount, Equilibrium Brewery opened in 2017 at 4 South Street. Its founders met while working at an environmental engineering firm, which may explain beer names like Photon and Wavelength. If you’re hungry, its Bonfire restaurant serves Central Texas barbecue, including smoked brisket.
A few blocks away, Oak & Reed on North Street serves comfort food made with locally sourced ingredients. On Cottage Street, Clemson Bros. Brewery takes its name from a local family known for industrial innovations in the 1800s. Your pint comes with some city history.
And if old buildings interest you as much as good food, the Webb Horton mansion across town is worth a look. Completed in the early 1900s, it is now SUNY Orange’s Morrison Hall. Inside, you’ll find detailed woodwork, marble fireplaces, and a stained-glass window attributed to the Tiffany studio.
Erie Way Park is a good first stop for anyone already downtown. It hosts a farmers market on Saturdays from 8 a.m. to 1 p.m., June through October. Nearby, Rail Trail Commons runs through the former Woolworth building and connects to the Heritage Trail.
The Heritage Trail follows the old Erie Railroad corridor and features a 10-foot-wide path for walking and cycling. The trail allows only Class 1 pedal-assist e-bikes. It was Orange County’s first multi-use trail and earned National Recreation Trail status in 2007. Near Chester, you can spot a half-mile stretch of track left over from the Greycourt rail yard.
If you’d rather start outside the city, the county lists parking lots at Ryerson Road in New Hampton and St. James Place in Goshen. The county doesn’t plow the trail in winter, but cross-country skiers and snowshoers can use it when there’s enough snow.
For a longer outing close to downtown, the Middletown Reservoir Trails cover more than eight miles of wooded paths around three reservoirs. Walkers, runners, and cyclists share the trails, and you might spot deer, foxes, or even a black bear. That last one probably isn’t on everyone’s hiking wish list.
For somewhere wilder, Highland Lakes State Park has more than 3,000 acres of woodland and lakes. The park has limited parking, no interior roads, and no restrooms, so come prepared. It also closes at sunset.
Hikers, anglers, horseback riders, and the occasional model airplane enthusiast share the park. Dogs are welcome on leashes no longer than six feet. The park also allows archery deer hunting in designated areas on certain weekdays, so check the park’s hunting map first.
A full day in Middletown could start at the farmers market and continue with a walk around the reservoirs. It could end with a film at the Paramount. Most of these places are close together, but you’ll need more than a pair of sturdy shoes to visit them all.
The Heritage Trail adds a second option. You could begin in one town and finish in another, stopping for lunch somewhere along the way. That gives you a good excuse to see more of the Hudson Valley rather than spending the entire day in one place.
You could also forget about fitting everything into a single visit. The Middletown area has plenty tucked between its older streets and wooded outskirts. The town has been around long enough to deserve more than a quick look, and Route 211 will still be there when you’re finished.
