Length: 11.2 miles

Elevation change: 1,128 feet

Nearby Towns: Peekskill, Garrison

Begin and End: At Bear Mountain State Park

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Winding atop the long, broad spine of Bear Mountain, Perkins Memorial Drive is best appreciated in the off-season. When the road is open to cars in the summer, you’ll ride shoulder-to-shoulder with them on their way to the top of the mountain. But wait until fall or spring — or even a mild winter day — to lift your bike past the bollards that close the road off to cars, and you’ll have the road to yourself.

I especially like the experience of getting to Bear Mountain State Park before sunrise, and biking to the top to watch the sun crest over the distant hills of Northern Westchester.

If you start out early enough, you’ll be alone on the mountain top’s broad meadow, with the heart of the Hudson Highlands spread out in front of you.

And perhaps most surprising and stunning to see, if the weather’s clear, is the glint of the rising sun on the sides of skyscrapers in far-off Manhattan. Riding out of the woods that embrace Perkins Memorial Drive, you can feel like you’re witnessing a mirage.

The Ride

At 1305 feet, Bear Mountain is the second-tallest mountain in the Hudson Highlands (Storm King is the tallest, at 1355 feet.) This route makes a gangly semicircle around the mountain, and is an out-and-back ride. All elevation gain is in the first half, and is easily navigated.

Park your car in the vast parking lot of Bear Mountain State Park, near the Inn, which re-opened to the public in 2011 after a six-year renovation. It’s worth a visit (even to use the bathrooms!): declared by The American Architect to be one of the “finest examples of rustic Adirondack architecture in America” upon its opening in 1915.

The Inn has a vintage dining room, complete with massive fireplace and mounted elk heads. The food here is hit-or-miss, but if you’re looking for a brew or drink, the bar does the trick. There’s also an outdoor balcony and a snack shop on the lower level.

Heading Up

From the parking lot, ride south through the lot towards the park’s head office, a rustic building in brown timber. Leave the parking lot and turn right onto Seven Lakes Drive. Shortly, you’ll come to a traffic circle. Take the first right off the traffic circle, and head uphill.

The road climbs steadily now, and in fact you’ll be climbing the entire way to the top. But it’s a gentle incline that electric and pedal-assist bikes will take easily.

The early part of this ride climbs through deep woods and past exposed rock ledges, as broad vistas of the Hudson River open up around you.

After climbing for a few miles, you’ll arrive at the turn-off for Perkins Memorial Drive, the road that leads to the tower and the top of Bear Mountain. In the off-season, this road is closed to cars. Lucky you! Just push your bike past the concrete bollards, and you’ll be on your way.

The road is silent now, and if you’re biking in the fall, it may be strewn with fallen leaves, unstirred by passing cars. I’ve witnessed more than a few bears poking through the underbrush alongside the road on this mountain, so keep an eye out. They’re more afraid of you, as they say, and I’ve found this to be true as they scramble to escape an approaching bike.

At the Top

When you reach the top, wander along the pathways that lead to scenic viewpoints over the river.

The view is perfect. To the east is the Bear Mountain Bridge, connecting the parkland with rocky Anthony’s Nose on the eastern shore. To the north is the river valley toward West Point and Storm King. You’ll find benches and boulders along the more precipitous terrain.

From the top, continue on for another mile to a dead-end roundabout. The views of the forested slopes across the valley open up intermittently here, and are worth a photograph.

There’s no other way back down the mountain but to retrace the route you came up. It’s a great time to slow down and appreciate the quiet beauty of this mountain and its forests, before grabbing a beverage at the old Inn.

These notes are descriptive only. You should always use the RideWithGPS app and/or download the turn-by-turn directions (provided above) for precise navigation.

The Details:

Elevation change: 1128 feet up the mountain; the climb is the first half of this ride (for 5.2 miles), then the second half is returning (downhill all the way) to the start. No part of this ride is overly demanding or strenuous on an electric or pedal-assist bike.

Direction: This is an out-and-back route up the mountain. The loop around Hessian Lake can be done in any direction.

Start and end: at Bear Mountain State Park, Route 9W North, Bear Mountain NY (GPS: 41.313052, -73.988650) The park has tons of parking (if you don’t go on a summer weekend, when it can be crowded), comfortable and clean public restrooms, and a gorgeous old hotel.

You’ll be charged a park fee if you get there in season or on the weekend. Therefore, I always recommend picking up an Empire Pass, a renewable entry pass for the state parks.

Afterwards:

If you’re not quite done biking, I recommend continuing the ride around Hessian Lake, on the north side of the Inn. A crushed stone path loops the lake, a mostly-flat, 1.3-mile trip at the lake’s edge. You’ll first pass the picnic area, then the buildings of the Overlook Lodge, part of the Bear Mountain Inn complex. On the lake’s western shore, a tall rocky ledge offers views of the entire crystalline lake and a place to sit for awhile.

The heart of the park is at the Bear Mountain Inn, the restored 1915 lodge and dining room. As I write this, the dining room — Restaurant 1915 — is closed due to the pandemic, as is the Blue Roof Bar, but I hope that as you read this, it’s reopened. While you might not feel like dropping 28 dollars for pasta after a bike ride, both lunch and breakfast there can be good and even creative, drawing ingredients and inspiration from local Hudson Valley farms.

You’ll also find the Hiker’s Cafe (also closed in the time of Covid) on the lower level of the Inn, where you can order up a beer, an ice cream, a sandwich or other snack after your ride. The Bear Mountain Trading Company, in the hotel’s main lobby is called the ; it’s fun to browse the limited selection of outfitting supplies as well as kitchy souvenirs and gifts. I especially like the Bear Mountain posters.

Cornwall, New York

Finally, one of my guilty pleasures is the car ride from Bear Mountain to Cornwall, New York, via the brilliant, scenic winding Route 218, the Storm King Highway. The road, when open, loops around steep, rocky cliffsides, dripping wet with mountain runoff, and lifts you up and over Crow’s Nest and Storm King Mountain on the west side of the river. You’ll find a scenic overlook on the right, with spectacular, sweeping views up and down the river. From here, the road continues at the edge of the cliff before descending back down into the historic town of Cornwall.

Once in Cornwall, you’ll find a quality brew at 2 Alices Coffee Lounge (311 Hudson Street), and if you’re there on a Sunday, the Painter’s Tavern (266 Hudson Street) serves a brunch that includes a veggie benedict, which I love. Check their Covid-related hours, and grab yourself a spot on the porch!

The rough, rolling hilltops of Bear Mountain State Park.

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