Our Favorite Hudson Valley Fall Foliage Drives!

There's something about a Hudson Valley October that makes you want to take the long way home. The maples along River Road start turning, the orchards fill up, and every farm stand between Rhinebeck and Tivoli suddenly has cider donuts on the counter. If you've been meaning to plan a fall drive this year, here are three of our favorite routes, a few timing tips, and what to toss in the back before you head out!

All three start right here in Rhinebeck, so you can grab a coffee in the village and be on the road in minutes Be sure to check out some of our dealership favorites including; All That Java, Bread Alone (Rhinebeck Village) or Mighty Donuts (Red Hook)!

When does fall color peak in the Hudson Valley?

Color doesn't arrive everywhere at once. The higher Catskill peaks to the west usually turn first, often in early October. Down in the valley near the river, towns like Rhinebeck, Red Hook, and Tivoli tend to hit their best color from mid to late October, depending on how warm and wet the season has been.

That spread actually works in your favor. If you miss peak up in the mountains, the river towns are often just getting going. New York State publishes a weekly fall foliage report during the season, and it's worth a quick look before you pick a weekend.

One more tip: weekday afternoons and early weekend mornings are the sweet spot. By midday Saturday the popular farm stands and overlooks get busy.

Drive 1: River Road and Route 9G to Tivoli

If you only have an afternoon, this is the one. It's short, easy, and packed with river views, old estates, and orchards.

Head north out of Rhinebeck and take River Road instead of the main highway. It winds past stone walls and historic estates, and the tree canopy along here is gorgeous once it turns. The landscaped grounds at Wilderstein are a nice first stop if you want to stretch your legs.

Keep going toward Red Hook and pull into Poets' Walk Park. It's an easy walk through meadows and woods that opens up to a wide view across the Hudson to the Catskills. On a clear October afternoon, it's hard to beat.

From there, hop over to Route 9G and stop at the Montgomery Place Orchards farm stand near the Route 199 intersection. They grow dozens of apple varieties, including heirlooms you won't find at the grocery store, and the stand typically stays open through Thanksgiving. Hours shift during the season, so check before you go. Then finish in Tivoli for an early dinner in the village.

Drive 2: Across the river to the Catskills

This is your early October pick, since the higher elevations turn first. It's also the most dramatic of the three.

Take Route 199 west over the Kingston-Rhinecliff Bridge. Slow down on the span if traffic allows, because the river views in both directions are worth it. Pick up Route 28 heading west from Kingston, and the scenery changes fast as the road climbs toward the mountains.

The Ashokan Reservoir is the highlight. You can walk along the water with the Catskill peaks reflected in it. Keep going toward Phoenicia for lunch and a walk around town before heading back.

Hikes along Route 28 for every skill level

One of the best things about this drive is how many great trails sit right off the road. Whether you want a flat walk with the kids or a real climb with a big payoff, there's something out here for you.

• Easy: Onteora Lake. Just a few miles west of Kingston, this is a gentle loop around a quiet lake, with old bluestone quarries tucked into the woods. The main loop is about two and a half miles, and you can add a couple of short side loops if you're enjoying yourself.
• Easy: Ashokan Rail Trail. A wide, flat, crushed stone path along the north side of the reservoir. It runs about eleven and a half miles end to end, but you can go out as far as you like and turn around. It's accessible for strollers and wheelchairs, too.
• Moderate: Giant Ledge. Take Route 28 to Big Indian, then head south on County Route 47. It's under three miles round trip with about a thousand feet of climbing, and it rewards you with a string of open ledges looking out over the valley. It's one of the most popular hikes in the Catskills for good reason, so arrive early.
• Challenging: Mount Tremper. A steep, rocky climb near Phoenicia to a steel fire tower you can climb for a 360 degree view of the fall color.
• Challenging: Wittenberg Mountain. A long, tough day hike from Woodland Valley with nearly 2,500 feet of climbing, and one of the best views of the Ashokan Reservoir from above. Save this one for experienced hikers.

A couple of quick tips for fall hiking: daylight goes fast in October, so start early and toss a headlamp in your pack. Trailhead lots fill up on nice weekends, too. The Catskills Visitor Center right on Route 28 in Mount Tremper is a handy stop for trail maps and current conditions.

Cell service gets spotty once you're deep in the mountains, so download your maps before you leave.

Drive 3: Back roads east to Pine Plains

If you'd rather skip the crowds entirely, head east. The farm country between Rhinebeck, Milan, and Pine Plains is rolling, quiet, and full of color, and you'll often have the road to yourself.

Follow Route 199 east and take whatever side roads look interesting. Some of the prettiest stretches out here are gravel farm lanes lined with maples and old barns. Pine Plains itself is a small, friendly village, and there are several farm stores nearby selling local dairy, meat, and produce.

If you're up for a short but steep hike, the trail to the Stissing Mountain fire tower rewards you with a view over the whole area. Afterward, you can loop back toward home on the Taconic State Parkway, which is one of the most scenic parkways in the state this time of year.

Before you go

A little prep makes the day a lot smoother. Here's what we'd pack and plan for:

• Layers. October mornings can be chilly and afternoons surprisingly warm, especially at elevation.
• Cash. Plenty of small farm stands are cash only or run on the honor system.
• Room in the back. Leave space for pumpkins, apples, and cider jugs. A small cooler helps if you're buying dairy or meat.
• A full tank. Gas stations thin out on the back roads and in the mountains, so fill up in town before you go.
• Offline maps. Download them ahead of time for the Catskills route.
• Extra following distance. Wet leaves on the road can be as slippery as ice, especially on shaded curves.

You don't need anything special to enjoy these drives. Most of the mileage is paved, and any well-maintained car will do just fine. That said, if you like exploring those gravel orchard lanes or you're heading out after a rainy week, all-wheel drive and a bit of extra ground clearance do add some peace of mind. It's one reason you'll see so many Subarus parked at farm stands around here. Every Outback comes with Symmetrical All-Wheel Drive and 8.7 inches of ground clearance, with 9.5 inches on the Wilderness trim.

Fall foliage FAQ

When is peak fall foliage near Rhinebeck?

The river towns around Rhinebeck usually see their best color from mid to late October. The higher Catskill peaks to the west typically turn a week or two earlier, often in early October.

Which drive is best if I only have a few hours?

River Road and Route 9G up to Tivoli. It's short, stays close to Rhinebeck, and includes a river overlook, historic estates, and a great farm stand.

Do I need all-wheel drive for these routes?

No. Most of these routes are paved and fine for any well-maintained car. All-wheel drive can add confidence on gravel farm lanes and on roads covered in wet leaves, but it isn't required.

Are there good hikes along the Catskills drive for beginners?

Yes. Onteora Lake and the Ashokan Rail Trail are both easy and close to Route 28. Giant Ledge is a great next step for moderate hikers, while Mount Tremper and Wittenberg Mountain are better for experienced hikers.

How can I check current foliage conditions?

New York State publishes a weekly fall foliage report during the season that shows how far along the color is by region. It's the easiest way to time your trip.

How do I avoid the crowds?

Go on a weekday if you can, or get out early on weekend mornings. The back roads east toward Pine Plains are also much quieter than the river route or the Catskills.

Enjoy the drive

Fall in the Hudson Valley goes by quickly, so pick a route, grab a coffee, and go see it while the color lasts. And if you're curious how an Outback or Forester feels on these roads, we're right on Montgomery Street in Rhinebeck and always happy to hand you the keys. Stop by Ruge's Subaru or give us a call to set up a test drive.