Towards the southern end of the parking area (near a dumpster), you’ll notice a triple blue blaze, which marks the start of the Lake Tiorati Trail. Proceed uphill on this trail to the ridge of Fingerboard Mountain, following the old route of Arden Valley Road for part of the way. At the top, turn left on the joint Appalachian Trail (A.T.) (white)/Ramapo-Dunderberg (R-D) Trail (red dot on white...
Hike Description:
Towards the southern end of the parking area (near a dumpster), you’ll notice a triple blue blaze, which marks the start of the Lake Tiorati Trail. Proceed uphill on this trail to the ridge of Fingerboard Mountain, following the old route of Arden Valley Road for part of the way. At the top, turn left on the joint Appalachian Trail (A.T.) (white)/Ramapo-Dunderberg (R-D) Trail (red dot on white), which follows a woods road past metal and concrete water towers and continues to climb along the ridge of Fingerboard Mountain on a footpath. You’ll reach a few false summits, one of which features an interesting balanced boulder. When the leaves are down, Lake Tiorati may be seen through the trees on the left.
About a mile from the start, you’ll reach a junction marked by wooden signs. Here, the blue-blazed Hurst Trail begins on the left. This trail leads down a few hundred feet to the stone Fingerboard Shelter, built in 1928. You may wish to take a short detour to check out this shelter, at which overnight camping is permitted.
Continue south on the joint A.T./R-D, which soon reaches another intersection. Here, the Appalachian Trail turns right, but you should follow the red-on-white blazes of the R-D Trail, which continues ahead along the ridge. The R-D Trail passes through attractive thickets of mountain laurel and hemlock. After reaching an open area, the trail descends rather steeply. At the base of the descent, watch carefully for the crossing of the Bottle Cap Trail, with its unique blazes – white bottle caps nailed to the trees.
Turn right onto the little-used Bottle Cap Trail, which traverses interesting terrain. Soon, you’ll notice a water-filled pit to the right of the trail, with a pile of mine tailings (discarded pieces of rock) just beyond. These are remnants of the Surebridge Mine, which was active during the Civil War. A short distance beyond, you’ll notice the remains of a banked stone structure on the left. More mine pits may be found to the south. For more information on this and other mines in the area, consult Ed Lenik’s book Iron Mine Trails.
The Bottle Cap Trail descends to cross the unmarked Surebridge Mine Road and, just beyond, Surebridge Brook. This crossing can be a little tricky if the water is high, and you may have to go a short distance upstream or downstream to find a good place to cross. After climbing steeply to the ridge of Surebridge Mountain, the trail bears left and overlooks the Surebridge Swamp, with Hogencamp Mountain visible In the distance beyond.
The Bottle Cap Trail descends through a dense hemlock forest, joins a woods road and ends at a junction with the joint aqua-blazed Long Path and red-triangle-on-white-blazed Arden-Surebridge (A-SB) Trail. Continue ahead on the woods road, now following the joint route of these two trails. In 300 feet, after crossing a wet area on rocks, the White Bar Trail leaves to the left. Just beyond, both the A-SB Trail and the Long Path turn right, leaving the woods road, and diverge. Continue on the A-SB Trail (red triangle on white), which takes the left fork.
Soon, you’ll notice a dramatic cleft at the edge of a cliff and reach a junction with the white-blazed Appalachian Trail (A.T.). Turn right, leaving the A-SB Trail, and follow the white A.T. blazes, which lead under an overhanging rock and into a fascinating rock formation, known as the Lemon Squeezer. The trail climbs through a very narrow cleft in the rocks at the base of the cliff and then goes up a steep rock face, where you will need to use both your hands and your feet. Those who are physically able to negotiate these challenges will find them to be a highlight of the hike. But if the climb is too difficult, it is possible to bypass the Lemon Squeezer by following a path to the left.
After reaching the top of the Lemon Squeezer, the A.T. continues on a more moderate grade to the summit of Island Pond Mountain. The stone ruins just north of the summit are the remains of a cabin built by Edward Harriman over 100 years ago. This is a good place to stop and take a break.
The A.T. descends from the summit and enters an attractive hemlock grove. After winding through the hemlocks, you’ll reach a junction with the aqua-blazed Long Path, marked by a wooden signpost. Continue ahead on the A.T., which soon parallels a stream, crosses it, then turns right and again climbs over the ridge of Surebridge Mountain.
At the base of the descent, the A.T. crosses Surebridge Brook and turns left onto Surebridge Mine Road. In a few hundred feet, you’ll notice a 100-foot-long water-filled mine pit on the right side of the trail, with a huge pile of tailings on the left side. These are the remains of the Greenwood Mine, opened in 1838 and last worked in 1880. At the north end of the mine pit, you can see drill marks in the rock face, and several rusted pipes are visible just north of the pit. You’ll want to take a break here to examine these interesting historical features.
Just beyond, where the A.T. turns right, leaving Surebridge Mine Road, you should bear left, continuing ahead on the unmarked mine road. You’ll recross Surebridge Brook but hardly notice it, as the brook goes through the rocks far below the surface of the road! Continue to follow the mine road past a marsh to the right, and look carefully for a huge boulder on the left, with a large tree growing against it. This feature marks the crossing of the aqua-blazed Long Path, which can otherwise be easily missed.
Turn sharply right, leaving Surebridge Mine Road, and follow the Long Path, which once again crosses Surebridge Brook and gently ascends a rise. Continue along the Long Path for another mile, crossing several intermittent streams and boulder fields, until you reach the paved Arden Valley Road, which is closed to vehicular traffic in the winter. The Long Path bears left here, but you should turn right and follow the paved road up to the crest of Fingerboard Mountain and then down to the Tiorati parking area where the hike began.
Publication: Submitted by Daniel Chazin on 01/27/2006

This loop hike traverses the ridge of Surebridge Mountain, passes by the historic Greenwood and Surebridge Mines and climbs through the narrow Lemon Squeezer.
Hike Checklist:
Whether you are going for a day hike or backpacking overnight, it is good practice to carry what we call The Hiking Essentials. These essentials will help you enjoy your outing more and will provide basic safety gear if needed. There may also be more essentials, depending on the season and your needs.
The Essentials
Hiking Shoes or Boots
Water - Two quarts per person is recommended in every season. Keep in mind that fluid loss is heightened in winter as well as summer. Don't put yourself in the position of having to end your hike early because you have run out of water.
Map - Know where you are and where you are going. Many of our hiking areas feature interconnecting network of trails. Use a waterproof/tear-resistant Tyvek Trail Conference map if available or enclose your map in a Ziplock plastic bag. If you have a mobile device, download Avenza’s free PDF Maps app and grab some GPS-enhanced Trail Conference maps (a backup Tyvek or paper version of the map is good to have just in case your batteries die or you don't have service). Check out some map-reading basics here.
Food - Snacks/lunch will keep you going as you burn energy walking or climbing. Nuts, seeds, and chocolate are favorites on the trail.
Sunscreen and insect repellent
Rain Gear and Extra Clothing - Rain happens. So does cold. Be prepared for changing weather. Avoid cotton--it traps water against your skin and is slow to dry. If you are wearing wet cotton and must return to your starting point, you risk getting chills that may lead to a dangerous hypothermia. Choose synthetic shirts, sweaters and/or vests and dress in layers for easy on and off.
Compass - A simple compass is all you need to orient you and your map to magnetic north.
Light - A flashlight or small, lightweight headlamp will be welcome gear if you find yourself still on the trail when darkness falls. Check the batteries before you start out and have extras in your pack.
First Aid Kit - Keep it simple, compact, and weatherproof. Know how to use the basic components.
Firestarter and Matches - In an emergency, you may need to keep yourself or someone else warm until help arrives. A firestarter (this could be as simple as leftover birthday candles that are kept inside a waterproof container) and matches (again, make sure to keep them in a waterproof container) could save a life.
Knife or Multi-tool - You may need to cut a piece of moleskin to put over a blister, repair a piece of broken equipment, or solve some other unexpected problem.
Emergency Numbers - Know the emergency numbers for the area you're going to and realize that in many locations--especially mountainous ones, your phone will not get reception.
Common Sense - Pay attention to your environment, your energy, and the condition of your companions. Has the weather turned rainy? Is daylight fading? Did you drink all your water? Did your companion fail to bring rain gear? Are you getting tired? Keep in mind that until you turn around you are (typically) only half-way to completing your hike--you must still get back to where you started from! (Exceptions are loop hikes.)
Check the weather forecast before you head out. Know the rules and regulations of the area.
The Leave No Trace Seven Principles
Plan Ahead and Prepare
- Know the regulations and special concerns for the area you'll visit.
- Prepare for extreme weather, hazards, and emergencies.
- Schedule your trip to avoid times of high use.
- Visit in small groups when possible. Consider splitting larger groups into smaller groups.
- Repackage food to minimize waste.
- Use a map and compass to eliminate the use of marking paint, rock cairns or flagging.
Travel and Camp on Durable Surfaces
- Durable surfaces include established trails and campsites, rock, gravel, dry grasses or snow.
- Protect riparian areas by camping at least 200 feet from lakes and streams.
- Good campsites are found, not made. Altering a site is not necessary.
- In popular areas:
- Concentrate use on existing trails and campsites.
- Walk single file in the middle of the trail, even when wet or muddy.
- Keep campsites small. Focus activity in areas where vegetation is absent.
- In pristine areas:
- Disperse use to prevent the creation of campsites and trails.
- Avoid places where impacts are just beginning.
- Pack it in, pack it out. Inspect your campsite and rest areas for trash or spilled foods. Pack out all trash, leftover food and litter.
- Deposit solid human waste in catholes dug 6 to 8 inches deep, at least 200 feet from water, camp and trails. Cover and disguise the cathole when finished.
- Pack out toilet paper and hygiene products.
- To wash yourself or your dishes, carry water 200 feet away from streams or lakes and use small amounts of biodegradable soap. Scatter strained dishwater.
- Preserve the past: examine, but do not touch cultural or historic structures and artifacts.
- Leave rocks, plants and other natural objects as you find them.
- Avoid introducing or transporting non-native species.
- Do not build structures, furniture, or dig trenches.
- Campfires can cause lasting impacts to the backcountry. Use a lightweight stove for cooking and enjoy a candle lantern for light.
- Where fires are permitted, use established fire rings, fire pans, or mound fires.
- Keep fires small. Only use sticks from the ground that can be broken by hand.
- Burn all wood and coals to ash, put out campfires completely, then scatter cool ashes.
- Observe wildlife from a distance. Do not follow or approach them.
- Never feed animals. Feeding wildlife damages their health, alters natural behaviors, and exposes them to predators and other dangers.
- Protect wildlife and your food by storing rations and trash securely.
- Control pets at all times, or leave them at home.
- Avoid wildlife during sensitive times: mating, nesting, raising young, or winter.
Be Considerate of Other Visitors
- Respect other visitors and protect the quality of their experience.
- Be courteous. Yield to other users on the trail.
- Step to the downhill side of the trail when encountering pack stock.
- Take breaks and camp away from trails and other visitors.
- Let nature's sounds prevail. Avoid loud voices and noises.
The Trail Conference is a 2015 Leave No Trace partner.
(c) Leave No Trace Center for Outdoor Ethics: www.LNT.org.