Woodstock’s Overlook Mountain Hike

The menu is vibrant and ever-evolving, vegetable forward, mediterranean inspired dishes made through a Hudson Valley lens. Think hearty grain bowls packed with roasted vegetables, flaky pastries filled with seasonal fruit, or rich coffee and tea served in handmade stoneware mugs. For breakfast, you might try their house-made granola with chamomile honey or a shakshuka style baked egg dish served in a bubbling tomato sauce. There’s also the pulled sesame bread topped with smoked salmon tartare and whipped cottage cheese—a fan favorite. Everything at Gemela is casual, seasonal, and elevated. It’s the kind of place where you pause, savor, and prepare for the trail ahead.

Just a short drive away up Meads Mountain Road lies the Overlook Mountain Trailhead. As you drive higher, the road narrows and the trees begin to thicken. The air cools. It’s clear you’ve left the town behind and are entering a more ancient kind of quiet.

The trail itself is a 4.6 mile out and back hike with a steady incline along a wide gravel path—ideal for hikers of all skill levels. It begins with a rhythmic ascent, shaded by tall trees and lined with mossy rocks. What makes this hike unique isn’t just the destination but the transformation that happens along the way.

We chose to hike barefoot, a grounding experience that changed the way we felt every step. The sensation of cool earth and sharp rock brought us into full presence. There’s something ancestral about walking this way. It invites you to slow down, notice more, and feel a deeper connection to nature.

About halfway up the trail, you’ll come upon the hauntingly beautiful Overlook Mountain House ruins. These remnants of a once grand hotel built in the 1800s stand like sentinels of time, now overgrown with ivy and softened by decay. It’s a surreal and cinematic moment, a ghost of another era that makes you pause, reflect, and maybe snap a photo or two.

From the ruins, the trail continues upward and narrows slightly. As you climb higher, glimpses of the valley below begin to appear through the trees. And then, suddenly, you’re there: the summit clearing.

At the top, the Overlook Fire Tower rises into the sky. For those unafraid of heights, climbing to the top rewards you with a 360 degree panorama of the Catskill Mountains and the Hudson River Valley. It’s awe inspiring. The air feels different up here, thinner, crisper, and somehow more alive.

The summit is a place to linger. Lay down a blanket. Pull out your journal. Share a thermos of tea with a friend. Or simply sit in silence and watch the clouds shift. Whether it’s solitude or companionship, the top of Overlook invites a moment of stillness that feels earned.

After making your way back down the trail, it’s time for a reward. Drive your Realcar a short distance back into town and make your way to Sweet Dreams Organic, an ice cream parlor that lives up to its name.

Located at 74 Tinker St, Woodstock, NY 12498, Sweet Dreams is a cozy haven for anyone with a sweet tooth and a love for local ingredients. The space is bright and welcoming, with colorful signage and smiling staff. Their ice cream is handmade, organic, and full of character.

Flavors rotate seasonally and is always a surprise. Think lavender honey, roasted strawberry, and lemon thyme. Even their classics, like vanilla bean or dark chocolate, taste more nuanced than usual. Each scoop feels intentional, crafted with love.

Grab your cone or cup and settle into the outdoor garden patio. Surrounded by greenery and shaded by trees, it’s the perfect spot to unwind. Here, your day slows once more. Birds chirp. The wind rustles the leaves. And you remember how good it feels to be alive.

No adventure is complete without the journey, and RealCar makes sure yours is as memorable as the destination. For our Woodstock trip, we chose the refined Land Rover Defender, a vehicle built for the winding roads and rugged paths of the Catskills. Its ride is smooth, spacious, and stylish, ideal for a full day escape.

But whether you choose a Defender, a sleek Mercedes Benz, or a sporty Porsche, our fleet ensures that getting there is never a chore. It’s part of the experience. Think of it as your private lounge on wheels.

From NYC, take I 87 North (New York State Thruway) to Exit 19 for Kingston. From there, continue west on NY 28 and follow signs toward Woodstock. Your first stop is Gemela, located at 8 Tinker Street. Once nourished and ready, head up Meads Mountain Road to the Overlook Mountain Trailhead at 353 Meads Mountain Rd, Woodstock, NY 12498. After the hike, circle back into town and visit Sweet Dreams Organic at 74 Tinker St, Woodstock, NY 12498. All three stops are conveniently close, making for a seamless and satisfying day trip. A day in Woodstock is more than an escape, it’s an experience. It offers a slower pace, richer flavors, and deeper breaths. It invites you to be present, from the first sip of coffee to the last lick of ice cream. And with RealCar, the journey is elevated at every turn. So go explore. Climb high. Taste everything. Drive well. This is your guide to one of the Catskills’ most unforgettable adventures.

Ready to hit the trail? Plan your escape at www.realcar.nyc.