Harlem Valley Rail Trail

My favorite bike ride

Without a doubt, my No. 1 favorite trail is the Harlem Valley Rail Trail (HVRT) in New York.

Many of the photos of farms and rural landscapes I post on Instagram are from this ride.

Why drive an hour north from Brewster up Route 22 for this trail in Dutchess County?

When you get there, you can breathe. It’s like a ride on an old quiet road that looks and smells like the country, whether it’s honeysuckle in the spring or pine in the fall. Some parts are in sun, but much is in dappled canopies of beautiful trees. 

There is hardly any grade to it and it’s generally well-paved, so it’s pretty easy. It’s usually not crowded, and folks you do meet are generally pleasant. It’s just a sweet ride that makes you happy to be alive and on a bike. And October can be a good time to ride: days are comfortably cool and the leaves are just turning.

I like to do this ride on weekends, for a few reasons. The Wassaic train station of the Metro North Harlem Line is the trailhead, and parking on weekends is free.

The trail is easy to spot, directly parallel to the tracks and Route 22. I ride north to Millerton from here, the oldest part of the trail. 

But from the train station, you’ll see a short stretch of trail that’s an offshoot of the HVRT. It takes you south about a mile to Wassaic hamlet, where you’ll find the Wassaic Project, an artists collaborative (with a Halloween event coming up), and an old-time restaurant-bar. Sort of a hipster vibe happening here.

I always head north to Millerton first, about 10 miles, and go to the hamlet on the way back if I’m up for it. Or just drive there.

The advantage to parking at the station is that you get a nice break when you get to Millerton. It’s like taking two 10-mile rides. Millerton gives you time to relax and stretch. There are plenty of bike racks, so you can walk through the compact village that’s loaded with cool shopping, food and browsing.

For instance: 

Oblong Books, a fun independent book shop with a dense kids section full of books, games and toys. There is an Oblong in Rhinebeck, too, but the first opened in Millerton in 1975. Go to the website to read why it was named Oblong. (An interesting bit of area history.)

Harney & Sons. Millerton Shop. This specialty tea shop has light lunch bites and a huge selection of top-notch teas in beautiful tins and a small gift shop with tea accessories and other quality, curated items.

Designer Finds. A high-end consignment shop with friendly staff and some good buys. Always a bag or two I’m tempted by.

Millerton Wines & Spirits. Unusual selection and good recommendations. I once bought a box of rosé that just barely fit in my backpack (I think it was two-litre), and I didn’t drink it till I got home, just FYI.

There’s also a vintage diner, and trendy clothing and furniture shops to fill the rest of your time. It’s a perfect break; you’ll be ready for the 10 miles back to Wassaic. Check ahead for hours; this is a big weekend place.

If you park in Millerton and head south, there’s not much to do at the train station, so it’s a bit harder for someone who doesn’t ride a lot. You don’t get a big respite. It’s like a full-on 20-mile ride.

If, on the other hand, you head north from Millerton to Copake Falls, also about 10 miles, you’ll be on the newer part of the trail.

The views are beautiful, and you’ll be in Taconic State Park for some of this ride. The trail is mainly smooth, but gets rough toward the northern end. And there’s not much to do at the northern end, either.

Along the ride, you can stop and read the historical markers. This was the site of an actual working railroad way back when.

The HVRT is still being developed and relies on grants and donations for progress. You can support the trail by becoming a member of the HVRT Association. 

It will eventually take you all the way to Chatham. When complete, the HVRT will be 46 miles long. Now that’s going to be a ride.