“An out-and-back of two long and burning hills with several incredible vistas as reward.
— Daniel Frisina
No bikes allowed from main trail down to Echo Lake, but it's well worth the 1/2 mi. walk on foot.
Big and long hill up a relatively smooth-ish and wide packed-stone path up to one of the most famous views of the catskills from the Overlook Fire Tower. Truly incredible up there. Views most of the way up to the west, Catskill Mountains in their full glory. But it is pretty heavily trafficked by hikers (to whom we always yield).
As far as fitness, it is uphill monotony at its best. No real intervals here, just up, up, up.
Then snake back down to the fork and make the mostly downhill, somewhat singletrack-like, to the Echo Lake fork. Less smooth, more leaves, and it is the north side of Overlook Mountain, therefore much more technical than Overlook Spur Trail. This trail gives you views a little more north. Big view reward being Indian Head Mountain and maybe even a glimpse of Twin Head Mountain.
Turn right off the main drag in Woodstock onto Rock City Rd and follow it 2.6 mi. (Rock City Rd becomes Meads Mountain Rd). Look right to find parking.
Sign in at the registration kiosk. It helps the DEC channel support for upkeep. The Fire Tower hill is the Red trail with numbered utility poles all the way up, called the Overlook Spur Trail. Then ride part of the Overlook Trail to the Echo Lake turnoff. This is the Blue trail.
Consider getting yourself a set of the New York-New Jersey Trail Conference maps of the Catskills. Waterproof and unparalleled in accuracy and scope of mapped terrain.
When parking at the Meads Mountain Road Trailhead, don't forget to look across the street at the glorious Tibetan Buddhist Monastery. Once you sign in, start your first trial-by-fire haul up the Overlook Spur Trail towards the Fire Tower. They occasionally have large utility vehicles maintaining the road and utility lines, so keep your wits about you. It is a manageable climb without a real need for any hike-a-bike. At the 0.35 mile mark, there is a small spring on the left of the trail (drink at your own risk, but people do it).
At 1.85 miles you'll reach the junction of the Overlook Trail (Blue) leading to Echo Lake.
Bear right and pedal another 1/2 mile and this leg summits at the peak of Overlook Mountain and some truly breathtaking views of not only the Catskills, but the Shawagunks, the Hudson River, and tons more. The Fire Tower has stairs and if you got the steam, it is well worth the climb up.
Coast back down the to the aforementioned fork and turn right onto the Overlook Trail (Blue) towards Echo Lake and Devil's Tower lean-to and Indian Head Mtn. This trail is more fun, more technical, but barely can be dubbed singletrack. It has more loose stone and a few big stone drop-offs. Just shy of a 1/2 mile in, look for another spring (and the muddy trail along it).
1.4 miles down and you'll reach the junction of the Echo Lake trail (Yellow). Remember, no bikes down that 1/2 mile to the lake, but it is a manageable walk (however dicey it may be in bike shoes).
When ready, turn around and start the second burly uphill back to the red trail. This is hard and long and technical uphill. Difficult to link the whole thing without a few foot taps, and maybe some heaving gulps of air.
Back to the fork, test your brakes (you'll need 'em), and descend pack to the parking area. Be wary of the multiple drain ditches/culverts, which amount to moguls/jumps at the speeds you'll be going.
From the NY DEC's website: "About two miles up the mountain from Meads Mountain Road Trailhead you reach the ruins of the third and last mountain house. The first mountain house, built in 1871 was destroyed by a chimney fire in 1875. The second mountain house, built in 1878, resembled a sanitarium for lung and tuberculosis patients, taking advantage of the high altitude clean air. In 1917 it was sold to financier Morris Newgold, but was again destroyed by fire in 1924. This time, it was rebuilt in concrete to become a grand hotel. However; it was never completed - a victim of World War II, changing public tastes, and the automobile. Since 1940, when it was boarded up, theft, vandalism, and nature have brought it to its present condition. It has been left as a ruin, slowly being reclaimed by nature. Please heed the warning signs and stay away from the structure"