Getting the Gunks Out

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Last year, I observed Bastille Day by riding to Philadelphia for a weekend with Sarah. We were met by two of my oldest and dearest friends, who travelled from Washington, DC, to meet us. I was never into doing “couple’s weekends,” but this one was easily one of the best weekends of my life. At the time, I regarded the weekend—consisting of a bike ride, perfect weather, a Bastille Day party, and some great exploring—as perfect.

Then it all fell apart. Sarah and I split shortly thereafter. To their credit, my DC friends still reach out occasionally to ask how I’m doing, but I am still reluctant to connect with them: it feels like I was expelled from the couples club, and I am too embarrassed to come around without a current membership.

For this year’s Bastille Day celebrations, I wanted to do something similarly epic to last year’s trip, but it seemed foolish to again ride to Philadelphia. My friend Brian, who I do a lot of long rides with, had a birthday this week, and we planned a three-day trip to New Paltz to ride around in the Shawangunk Range:

  1. Riding 80 miles to New Paltz
  2. Riding 70 miles around the Gunks
  3. Riding 30 miles to Beacon

Because you might someday want to do something like this, here are some details about the ride.

A Day on the Trails

There are three ways to get to New Paltz with your bike:

  1. You can drive there.
  2. You can take a Metro North train to Poughkeepsie and ride about 10 miles over the Walkway over the Hudson and along NY-299.
  3. You can bike there.

We elected to take the third option and rode eighty-plus miles from Woodlawn in the Bronx to New Paltz, almost entirely on paved, off-road trails.


We started the tour on the South Westchester County trail for about 13 miles to Elmsford. After riding along the streets of Elmsford, we connected to the North Westchester County and Putnam County trails that reach all the way to Brewster, New York. We didn’t take it quite that far because we connected to the Dutchess Rail Trail in Hopewell Junction.

To do that, we had go over a ridge with some fairly steep climbs. As far as we could tell, there was no way to avoid climbing. Ultimately, we rode on Miller’s Hill Road, with a 17% maximum grade, to clear the ridge.

Miller's Hill Road

And after reaching the top, we had to make a fairly steep, white-knuckle descent into East Fishkill.

Elevation profile 2jpg

Once we passed through East Fishkill and Hopewell Junction, we reached the Dutchess Rail Trail, a nicely paved and tree-lined path, that I first took almost four years ago to the date with Sarah en route from Cold Spring to Hyde Park.


It was a hauntingly bittersweet, thirteen-mile trip because I reminisced over that first ride—with all its ups and downs. Sarah had struggled as we climbed from Cold Spring to US-9, rode through the busy roads of Fishkill, and, because this was before I had a dedicated GPS unit, labored to find the trailhead in Hopewell Junction. But once we reached the trail, she had a much easier time and was in really good spiritsuntil she crashed just before reaching Poughkeepsie. I was ahead of her at the time and hadn’t noticed that she was shaken up until I backtracked to find her; I felt like a jerk for not being there for her. Riding through this stretch this year, I couldn’t help but feel guilty for speeding through the trail in 2015, as opposed to Sarah’s experience four years earlier.

The Dutchess Rail Trail ends in Poughkeepsie and connects to the Walkway over the Hudson, an old railroad bridge that spans the Hudson River between Dutchess and Ulster counties. It is also the longest footbridge in the world.

Walkway over the Hudson:Poughkeepsie :: High Line:Manhattan

I had biked there a week earlier, and noticed that it was a very popular recreational space. Its popularity presumably stems lovely views of the Hudson River from this high vantage.

Looking south at the Hudson River from the Walkway over the Hudson

Once on the west side of the Hudson, we connected to another bike trail—the Hudson Valley Rail Trail through the towns of Highland and Lloyd. After the trail ended, we followed NY-299 and roads with telltale names, such “New Paltz Road” and “Old Route 299,” to arrive at our destination, a hostel in New Paltz.

New Paltz Hostel

We selected this place for two reasons: it was cheap, and it was located right on Main Street. Being in town allowed us to enjoy a wonderfully cheap “dive” bar, a pleasantly rustic restaurant and cocktail bar, and Huguenot Street, the oldest continuously inhabited street in America.

Touring New Paltz

From Huguenot Street, I looked west and could see in the distance, the terrain for the following day’s ride: the Shawangunk Ridge.

Medio Fondo, Déjà Vu

Saturday’s ride along the Shawangunk Ridge was a repeat of a ride we had done a year earlier with another guy. Like last year, we followed the Medio Fondo route of the apparently dormant Gran Fondo Gunks, an organized ride that was evidently cancelled for 2014.


At 68 miles and about 4,500 feet of vertical gain, it is exactly what I would consider a comfortably long ride. It included some rolling hills, which is my favorite terrain, and two 1,000-foot climbs.

Elevation profile

We biked from Pine Bush and Walker Valley along NY-52, ascending about 1000 feet over three miles to the summit in Cragsmoor. We descended slightly to get a view of the valley and pose for self-indulgent portraits.

Climbing Cragsmoor

Continuing on NY-52, we reached Ellenville, a town that features a vacant storefront that was once home to the local weekly news website and newspaper.

Climbing Cragsmoor

After a brief lunch, we proceeded west to Minnewaska, the second long climb of the day.

Climbing Minnewaska

One notable difference from last year’s ride was that Rough Cut Brewery, the brewery I spotted last year but was closed, was in fact open for business this year.

Climbing Minnewaska

The only drawback was that they didn’t open until 4:00 PM, and we pedaled by it at about a quarter to one o’clock. Bummer.

We detoured from the 2014 route by circumventing the town of Rosendale. Last year, we found that despite all the climbing we did, the steepest climb of the day was through this town. This year, we routed around the town and took the Walkill Valley Rail Trail, which ascends over town and provides some very lovely views.

Walkway over Rosendale

For most of the ride, the weather was cool and cloudy, but punishingly humid. By the time we reached the end, the sun had broken through the clouds and ushering in temperatures approaching 90°. My fellow “epic-riding brah” insisted we repeat last year’s finish by swimming in the Ulster County Pool to cool off. I was hesitant at first because I was sore and exhausted and wanted to grab a shower and food. But in the end, I capitulated. And he was right: a swim on a hot day, after a long day on the bike, was exactly what I needed.

Beckoned Back to Beacon

The last ride of the weekend, a thirty-plus–mile ride from New Paltz to Beacon, was “epic” only because of the heat. Temperatures reached the low-90s, which was the hottest day we had all summer. We benefitted from taking the tree-lined Dutchess Rail Trail back to Hopewell Junction. From there, we headed south and west, along NY-82 and NY-52, through Fishkill and on to Beacon.

We finished our ride to Beacon at The Hop, a place that I had first visited on Bastille Day 2013. During my earlier visits to The Hop, it was a beer store with a tap room and a small kitchen. Since then, they have decisively expanded. They moved about a quarter-mile up Main Street to a sprawling space that includes a bar, two dining rooms and a fairly large beer store.

The Hop in Beacon

A quick descent down Main Street, through various places I had visited on earlier trips to Beacon, ended at the Metro North station. From there, I enjoyed a last look at the Hudson River on this trip.

Hudson River from Beacon Station

And I looked forward to the next time I come here to visit… with or without a bike.

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