Compilation of Winter Gravel Rides

We typically post fewer rides in the winter and most tend to have a single pace group, rather than our larger “three speeds” rides. This usually means participants from our “long distance” (i.e. faster) pace group. Here are some quick ride reports from some of those winter rides. You’ll find route links for all of them.

Sunken Mine is Back! [Fahnestock / Cold Spring Gravel]

This was a last-minute solo ride to scout conditions in areas that had become unrideable due to storm damage. Fortunately Sunken Mine Rd is back in action. Bell Hollow road/trail, however, remains a mess! Avoid that one if possible.

From my Strava post:

What a beautiful winter day for a gravel ride! Only 58 miles, but the route had some zing, including the fun triple set of climbs: Miller Hill -> Long Hill Rd -> E Mountain Rd . In my mind, cool weather equals climbing weather – at least when I can manage to escape Long Island! Overall, an excellent ride – made better with awesome cookies for fuel – courtesy of Kathy.


Steve’s Strava Post:

Freshly repaired Sunken Mine Rd.

New Year’s Eve Spectacular (Dover Plains)

Awesome New Year’s Eve gravel ride in Dutchess County, NY! It was beautiful out there today. A little chilly, but really not bad once we got moving. Thank you to everyone who came out to ride! I forgot to get a group photo at the start – we had to get moving to warm up, ha ha! Next time.


Steve’s Strava Post:

Enjoying some car-free miles on closed-for-the-season dirt roads in Dutchess County. Just make sure the snow has really melted! It takes a lot longer back in the woods and without car traffic!

Great winter riding — we kept moving to stay warm.

GrNY: Frozen Gravel from Katonah

Lovely ride in Westchester County, NY! We had bright sunshine, clouds, calm air, blustery winds, and some short snow flurries. And then bright sunshine again! Dirt roads were in decent shape (a bit of mud in places, but not bad), paved roads 98% good with a few random bits of ice to avoid. And we traveled many quiet country roads through woods, horse country estates, etc. Thank you to everyone who showed up to ride on this chilly day!


Steve’s Strava Post:

Group photo at the start in Katonah.

We had a little bit of snow in the latter part of the ride, but not much.

Cold Spring Gravel (Reversed) – And YES, there is still snow on Sunken Mine Rd

A return to the nearby Cold Spring area in Putnam County, NY. Wow, what a beautiful winter day! The sun was shining for our entire ride. We had a great crew of riders, a few of whom chose the shorter route to get back a bit earlier. And we had a bit of extra adventure when we hit Sunken Mine Rd. I stated in the ride invitation “We are hoping Sunken Mine will be snow free, but we’ve been surprised before!”. SURPRISE! There was definitely some snow and ice, ha ha!

Overall, it was a great day on the bike with plenty of climbing to keep us warm (and provide a humble average speed despite our efforts on the hills!). If you choose to travel in this direction, know that you will hit the two biggest climbs, back-to-back, during the last part of the ride. We chose this direction so the folks who were leaving early could maximize their time on dirt before peeling off. It worked out just fine.


Steve’s Strava Post:

Super Bowl Gravel from Katonah

This ride was on Super Bowl Sunday. it was a “three speed” ride, with warm weather (for winter) so we had a great turnout. There were a few places where the ground was sticky and velcro-like, but conditions were good overall considering yesterday’s rainfall in this area. A bunch of riders hung out for beer and/or food at Paulie’s Deli after the ride. Paulie’s has some good beer on tap and more options in the refrigerator case. A big thanks to everyone who joined us today and made it a fun ride!


Group photo from Super Bowl Sunday ride.

Some of the long distance group out on the road.

Dirt Roads and Killer Climbs from Peekskill (Abridged due to rain)

Yet another return to the Cold Spring area, but starting from Peekskill. Why a return? Rain was in the forecast, so we needed to start someplace close and Peekskill was ideal. It’s a very short train ride or drive from NYC and other places nearby, so we could get an early start.

Beautiful forested roads, fun twisty up-and-down descents, and far more dirt than pavement. It was a good day on the bike with some great company. Thank you to everyone who came out for this climb-fest! For folks who haven’t done as much riding yet this season, it was quite a way to get rolling again! While we didn’t do the 79mi/10,000ft version, even this smaller version had some zing. Some of us grabbed beer and tacos, which were extra enjoyable after a challenging ride!

Steve’s Strava Post:

ROUTES (We did the shortest one to avoid the rain).

54 mi, 6200 ft (5400 ft on RWGPS) “Stay closer to the cars/train” option:

67 miles and possibly 8700 ft (7600 ft on RWGPS)

79 miles and possibly 10,000 ft (8800 ft on RWGPS)

Staying warm on the hills!

End of Season Ride: The rest of the dirt roads in Westchester!

Two weeks ago, we did a ride that included *most* of the reasonably connectable dirt roads in Westchester County (see: This week, we polished off the rest of them! We had a great group of riders, including a number of new faces. Thank you all for joining us today!

We declared this to be an *End of Season* ride. And what an excellent season it has been! We started the season with our Spring Gravel Series: five weekends in a row of awesome rides covering all of the “gravel regions” within ~1.5 hours drive of NYC. A true gravel tour! We continued with group rides every other week through today (November 12).

What does the “off season” mean for Gravel NY? Check out Jay’s post on Strava for more details:

The short version: GrNY rides will be much less frequent over the winter. Rides might have a single pace group, instead of “three speeds”, where all the groups overlap several times and hangout at the end. Rides will typically be announced with less notice due to unpredicable weather. We may do some paved riding to avoid messy freeze/thaw conditions on dirt roads and trails – or just for some variety. If we don’t see you this winter, we look forward to riding with you again in the spring!

Parts of the Long and Medium distance pace groups connecting just outside of Mountain Lakes State Park. Both groups were taking a short breather (and waiting for riders) after tackling the largest climb and roughest trails of the day!

This photo is courtesy of Anthony (AKA ToneB). There was still fall color in the understory in some places.

Oct 28, 2023: Almost all the dirt roads in Westchester!

Our goal was to ride all the dirt roads in Westchester County that could be connected without too much pavement in between (>90% of the total). We wanted this to be a gravel ride after all! We almost succeeded in our mission, but apparently we missed the northernmost loop. I was wondering why we came up about 4 miles short. I guess we’ll need to try it again in the spring season! Overall, It was a lovely ride on a day that seemed too warm to possibly be in late October. Thanks for joining us on this silly mission!

Here’s the full route:

50-mile route that overlaps the big route. A number of people opted to ride this shorter distance version:

Steve’s Strava Activity (we missed the northern loop!):

A bit of background:

  • We did an “All the Dirt Roads in Westchester” ride in 2021. We probably covered ~95% of the reasonably connectable dirt roads in the county in about 100 miles and 10,000 ft climbing. It was a crazy, spaghetti-like route!
  • This updated route condenses the footprint of the ride to make it more dirt-heavy (>50% gravel) at the expense of losing a few dirt road segments. You should still expect a bit of routing insanity! (loops, out-and-backs, etc). Caveats: Short dead end streets, isolated road sections, and some small pieces of longer roads were skipped to make the route a little less crazy and to keep the proportion of dirt very high.

Skipped dirt road segments include:

  • Boway/Woodway and Boutonville/Dingee roads: Requires a pretty big pavement-heavy loop for minimal increase in dirt road coverage.
  • Black Spring/Black Brook: Tiny segments of dirt that add too much pavement.
  • Millertown Rd: Only a tiny segment is still dirt, since half of it has been paved.
  • Byram Lake/Oregon Rd: Too isolated. Requires too much paved riding to get there and back.
  • Various small pieces of longer dirt roads: In other words, you’ll visit most of a given dirt road on this route, but might skip a small segment to make the route connect more readily with other dirt roads.

Riders on the “medium” version of the route leaving the Market at Union Hall.

The pond in Mountain Lakes Park, which was just before our biggest (and most technical) climb of the day. The park road is in much worse shape than it was earlier in the season, so use caution on the way up! And I strongly advise against riding down it on a rigid gravel bike. You’ll easily get too much speed for the rocky conditions and the potentially slippery leaves covering the road/trail.

Oct 22, 2023: Autumn Ride from Pawling, NY

We encouraged folks to “join us while you can!”, and many people came out to ride. Days are getting shorter and temperatures are dropping. We don’t know when the best riding weather will end for the season.

This was a beautiful ride with cool weather, gorgeous autumn leaves, and a great group of riders. We revisited our Spring Gravel Series route that starts in Pawling, NY and travels through Litchfield County, CT. It was great to return to this region for the fall colors. After the ride, people from all three pace groups gathered at O’Connor’s Public House for food and drinks. Thank you everyone who joined us for this spectacular day!


Steve’s Strava Activity:

Long-distance group riding through forested dirt roads.

Part of the medium-distance group (with Kathy behind the camera).

Beautiful views with fall foliage.

Long-distance group stopping for a photo at Mud Pond. The pond is much more beautiful than its name would suggest!

Oct 8, 2023: Goldens Bridge to Carmel Hamlet

Fantastic ride in Westchester County with a fun group! We started at Goldens Bridge, but traveled north towards Carmel Hamlet and the beautiful Croton Falls and Middle Branch Reservoirs. These routes have less intense climbs than we did on our previous “three speeds” ride in Cold Spring, but you should still expect some hills.

Overall: There were lots of reservoirs, leaves turning color, forested roads and horse country estates. The dirt roads were mostly in very good shape for riding, with just a few wet spots from yesterday’s rain. The weather was great, too. A little cool, but very comfortable. Most people stayed after the ride to hang out over cold drinks and food (i.e. tailgating at Goldens Bridge Station, which is across the street from a supermarket and a few stores). A fun time!

-Long (66mi/>4800ft):
-Medium (59mi/>4200ft):
-Short (45mi/>3200ft):

Steve’s Strava Activity:

Some of the medium-distance group near the Croton Falls Reservoir.

Some of the shorter-distance group on the Cross River Dam.

Lots of fall color on the trees.

Riders on the hard-packed dirt roads of Westchester County.

Oct 1, 2023: Gravel Century – Mt Riga, Sunset Rock and the Berkshires

This was the second year that we’ve done this ride (previously in 2022). It needs to become an annual tradition! This is some of the best riding in our broader region. Absolutely worth the trip and the effort. Note: You’ll need a car (or a lift from another rider) to get to the start location.

Ride description: Epic gravel ride that includes the climb up Mt Riga (~1250ft), the more challenging climb to Sunset Rock (~1050ft, but considerably steeper), the flat (and beautiful) Housatonic River Road, and other premium stretches of gravel in the region. It includes the option to visit Bash Bish falls (the trail is just steps away from the route). This can easily be made into a two-day bikepacking adventure (camping overnight at Taconic Falls State Park). Worth the drive!

Itinerary for our ride.
-19.5 mi: Optional water/gatorade stop at LaBonne’s Market in Salisbury
**34.5 mi: Required stop at Depot Deli for snacks/food/water. This will be needed after climbing Mt Riga and before climbing Sunset Rock (each 1250ft and 1050ft, respectively). Bathrooms potentially available at Taconic State Park campground across the street (when open for the season).
**49 mi: Lunch or snacks at one of these places: a) The Marketplace Kitchen and Cafe in Sheffield (sandwiches, etc, but extremely slow service); b) Gulotta’s Convenience Store next to the Mobil Gas Station has sandwiches, gatorade, etc, but no batherooms!; c) The Bakin’ Bakery (good place for desserts, they had small bottles of gatorade, and a bathroom).
-65mi: Optional detour to Falls River Cafe.
**78: Required Stop at supermarket or gas station in Sharon, CT. Last reliable place to get food/drinks before end of ride. Gas station = no bathrooms. But the supermarket across the street has bathrooms.

Parking: Housatonic Meadows Picnic Area has been a safe choice. They had a decent pit-style toilet (no running water) when we last visited (Oct 2023). There is no fee (just drive and park — no booth). Mark’s ride starts at Housatonic High School. I’m guessing that will work for weekends or summer, only.

Too long? Try these still epic, but shorter options. The shorter routes include both big climbs and the Berkshires sections.


Shorter versions:

Steve’s Strava Activity:

Our route includes an abundance of quiet dirt roads (~50%) and generally nice paved roads connecting it all together.

Great views across our ride.

Warnings about damaged dirt roads and trails in our region

Areas north of NYC experienced torrential rains during a mid-July storm (2023). It’s already mid-September, but some roads and trails have not yet been repaired. Be extra careful if you plan to ride in these areas, below.

Parts of Sunken Mine Rd, in Puntam County, NY were destroyed during the aforementioned storm. I’ve heard from a few groups of riders who found this out the hard way. In one case, a rider went down pretty hard as they approached the destruction. Even on the “better” parts, I’ve heard that the road/trail is pretty rough and there are many downed branches. The photo above the post, with the rider in yellow, is of Sunken Mine Rd. It was taken by Ken shortly after the July storm. Thanks Ken!

NOTE: Many of the dirt roads in Putnam County are in rougher shape than usual. On our last ride, we encountered many more washouts, big potholes, or soft spots (where riders lost traction) than usual. Old Albany Post Rd is one example of a great dirt road, which is rideable, but extra caution is required – particularly when going downhill, where speeds will be high. We purposly routed uphill only for most of our time on that road, with one short exception, which you could consider cutting around by staying on Rt 9 in that direction.

Black Rock Forest is a beautiful place to ride. That said, it should be avoided by bike until the roads and trails can be repaired (consider a hike instead). The trails and some of the other infrastructure at this research forest were badly damaged in that July storm. I think some of that damage will take a long time to repair. Note: bikes are only allowed on the roads / jeep roads — see their trail maps. Currently, trails are open for hiking but they state: “Please exercise extreme caution on trails and roads, and especially stream crossings!”. Has anybody been to Black Rock Forest recently and ridden on the bike-allowed trails? It would be great to understand current conditions.

Storm King Highway still has a section that was washed into the Hudson River. Yes, this is a paved road, but it is also the main way to travel through that area, on a bike, without riding on the side of the highway (9W) with an intermittenly disappearing shoulder (the shoulder turns into a drainage culvert in places), which I do not recommend. You will *not* be able to walk around that destroyed part. One section of the rear slope is a sheer rock face with water running down it, like a waterfall that is ready to carry you down the cliff.

Know about other damaged dirt roads we should watch out for? Let us know! email: In particular, we tend to ride in these areas, which are within striking distance of NYC: Westchester, Putnam, Orange, and Dutchess Counties in NY; Litchfield County in CT; and the Bedminster region in NJ. Thanks!

The photo below is the state of Storm King Highway as of recently (September 2023). I’m not going to provide a photo credit since you aren’t supposed to visit that spot. The waterfall-like section is not visible in the photo, but please understand that you will not be walking around this mess. You will be stuck on one side or the other.

Sept 16, 2023: Putnam County Dirt!

On this wonderfully cool Saturday morning, we tackled a fun and challenging set of routes that included many of the big climbs in Putnam County. We modified our original routes to avoid some dirt road sections that were badly damaged in a storm in July (particularly Sunken Mine Rd), but we still traversed some beautiful terrain.

The long route, unlike our Spring Gravel Series version, saved the two largest climbs for the last 1/3 of the ride – and we might have broken a couple of riders with that setup – sorry! Those two big climbs are tough at any time, but especially difficult after you’ve already done 5000 ft of climbing. The route was mostly downhill for the last ~10 miles if that counts for anything.

Many riders stayed to hang out over cold drinks and food after the ride, which was fun. Our long-distance group missed a few people before they headed off (we got back a little behind schedule). For the record: Kathy (medium group) and I (long group) had almost the exact same moving time, 4:14 and 4:15, so our planning was actually pretty good. That said, we ended up taking some longer pauses in the long distance group for a variety of reasons, which slowed things down a bit.

-Long (v2):
-Medium (v2):
-Short (v2):
Note: We’ll update these routes, particularly the long distance route, when Sunken Mine Rd is repaired again. The long distance route included a lengthy stretch along Rt 301, which was “acceptable”, but not as nice and quiet as the rest of the route.

Steve’s Strava Activity:

Speeding along dirt roads through the woods.

Riders from the long distance group taking a pause before the biggest climbs of the day.

Part of the medium distance group, stopping to regroup.

Sept 2, 2023: Jersey Dirt! From Natirar Park

We revisited another of our Spring Gravel Series of routes. Once again this was after a three month absence. This time the beautiful Bedminster area of New Jersey was our target. If you haven’t ridden here, it is worth the drive or train ride to experience it. This area of NJ has some of the nicest gravel riding in our region: Dirt roads through woods, forests, and along peaceful streams; Ridges and hills with beatiful pastoral views; Quaint small towns with General Stores. You’ll find at least one cooler in the woods with local maple syrup and an on-your-honor jar for depositing money.

We started from the lovely Natirar Park (named after the Raritan River, but spelled backwards, however you might feel about that). We had an awesome ride with a fantastic group. Highlights included the rugged climb up the Teetertown Ravine, the spectacular Lockwood Gorge – and of course many beautiful country roads through farm and forest. We saw some wildlife, too, including a bear and it’s two cubs (thankfully off the side of the road – so we could avoid getting between them!). Just about everyone hung out after the ride for cold drinks and snacks. As always, thank you to everyone who joined us and made it such a fun ride!

ROUTES (Same as our 5th Spring Gravel Series – These awesome routes deserve to be ridden more than once!)

Long (62mi, 5000ft):

Medium (52mi, 4400ft):

Short (45mi, 3700ft):

Also: Steve’s Strava activity

Long-distance group on the road.

Medium-distance group traveling through the beautiful Lockwood Gorge.

Long distance group again.

Most of us walked the two short rocky sections in the Lockwood Gorge. These short hike-a-bike areas (a few hundred yards) are well worth it to enjoy the rest of the scenic (and rideable) parts of this closed-to-cars former dirt road.

Aug 19, 2023: Dutchess Dirt

On Saturday, August 7 the GrNY group returned to Dover Plains after a three-month absence. As expected, it was worth the drive or train ride! We had three pace/distance groups (long, medium, short) who traversed the picturesque dirt roads of Dutchess County. We were fortunate to get absolutely perfect weather, too! After the ride, everyone celebrated with food, drinks and/or ice cream at Kelly’s Creamery and Kelly’s Husband’s Food Truck.

The medium-distance group did our less-intense variant of the classic Dover Plains Dirt loop (i.e. this route: This medium-distance variant (link further down) is possibly the best version. It skips the two steepest climbs in favor of other great dirt road riding. It also adds more civilization, including better food options in Amenia, NY and Sharon, CT. It uses a spur of the Harlem Valley bike trail to connect it all together and adds some new (flatter) dirt/gravel roads make up for any lost dirt, including the always lovely (and well-graded) climb up Deep Hollow Road.

The short-distance group did the same route, but stayed on the Harlem Valley Rail Trail at the midway point. This made for a shorter but also extremely pleasant ride back to the start. Finally, the long-distance group did a very different route that cut westward and traversed the area around the Wassaic Multiple Use Area (a lovely forested area).


Macedonia Brook State Park

Medium-distance group on the road

Boardwalk through a beautiful wetland (only traversed on the short-distance route).