How to Hike the Hickory Hill Trail

The Hickory Hill Trail is one of the most beloved and rewarding hiking experiences in the northeastern United States, offering a unique blend of rugged terrain, panoramic vistas, and rich ecological diversity. Located just outside the historic town of Millbrook, New York, this 4.7-mile loop trail winds through mature hardwood forests, across babbling streams, and up to a rocky summit that provides one of the most breathtaking 360-degree views in the region. Whether you’re a seasoned backpacker or a weekend hiker seeking solitude and natural beauty, the Hickory Hill Trail delivers an unforgettable journey.

Unlike many popular trails that suffer from overcrowding, Hickory Hill maintains a quiet, immersive atmosphere thanks to its lesser-known status and moderate difficulty level. This makes it ideal for those looking to disconnect from digital noise and reconnect with the rhythms of the natural world. But to fully appreciate—and safely navigate—the trail, preparation is essential. This guide provides a comprehensive, step-by-step walkthrough of everything you need to know to hike the Hickory Hill Trail with confidence, from trailhead logistics to environmental stewardship.

By following the advice in this guide, you’ll not only enhance your personal experience but also contribute to the long-term preservation of this fragile ecosystem. The Hickory Hill Trail is maintained by local volunteers and protected under conservation easements—your responsible behavior ensures future generations can enjoy its splendor.

Step-by-Step Guide

1. Research the Trail Before You Go

Before packing your bag or stepping onto the trail, invest time in understanding the Hickory Hill Trail’s layout, conditions, and seasonal variations. Start by visiting the official website of the Millbrook Land Trust (millbrooklandtrust.org), which manages the trail. Here, you’ll find updated trail maps, recent condition reports, and seasonal closures.

Key details to note:

• Trail length: 4.7 miles (loop)
• Estimated time: 3 to 4.5 hours
• Difficulty: Moderate to challenging (due to elevation gain and uneven terrain)
• Trailhead coordinates: 41.7522° N, 73.7411° W
• Trail markers: Blue blazes (occasionally faded—carry a map)

Download the trail map as a PDF and print it, or save it offline on your smartphone using apps like Gaia GPS or AllTrails. Do not rely solely on cell service—coverage is spotty beyond the parking area.

2. Choose the Right Time of Year

The Hickory Hill Trail is accessible year-round, but each season offers a distinctly different experience.

Spring (April–May): The trail is lush with wildflowers—trillium, violets, and lady’s slipper orchids bloom in abundance. However, early spring can bring muddy sections, especially near the creek crossings. Waterproof boots are strongly recommended.

Summer (June–August): This is the most popular season, with long daylight hours and full canopy cover providing shade. Be prepared for high humidity and insects—especially mosquitoes and ticks. Start early to avoid afternoon thunderstorms, which are common in the Hudson Valley.

Fall (September–October): Arguably the best time to hike Hickory Hill. The maple, oak, and hickory trees transform into fiery reds, oranges, and golds. The air is crisp, the trails are dry, and wildlife is active. Crowds increase on weekends, so consider hiking on a weekday.

Winter (November–March): For experienced hikers only. Snow and ice can make the rocky sections treacherous. Microspikes or crampons are essential, and trekking poles are highly recommended. The summit view is unparalleled when dusted with snow, but daylight is limited—plan to finish by 3:30 PM.

3. Prepare Your Gear

Proper gear turns a good hike into a great one—and can be lifesaving in emergencies. Here’s a detailed checklist:

• Footwear: Sturdy hiking boots with ankle support and aggressive tread. Avoid sneakers or trail runners unless you’re experienced and the trail is dry.
• Backpack: A 10–20L daypack with a hip belt to distribute weight evenly.
• Hydration: At least 2 liters of water per person. Consider a hydration bladder for easy access. A water filter (like a Sawyer Squeeze) is useful if you plan to refill from the stream near mile 2.5.
• Nutrition: High-energy snacks: trail mix, energy bars, dried fruit, and nuts. Bring more than you think you’ll need.
• Navigation: Printed map, compass, and GPS device or smartphone with offline maps. Don’t assume your phone will work.
• Weather-appropriate clothing: Layering is key. Start with a moisture-wicking base layer, add an insulating mid-layer (fleece or down), and top with a waterproof, breathable shell. Even in summer, temperatures drop significantly on the summit.
• Trekking poles: Highly recommended for steep ascents and descents. They reduce knee strain and improve balance on rocky sections.
• First aid kit: Include bandages, antiseptic wipes, blister treatment, tweezers (for tick removal), and any personal medications.
• Insect repellent: DEET or picaridin-based spray. Apply before departure and reapply every 4–6 hours.
• Emergency items: Whistle, headlamp with extra batteries, emergency blanket, and a small multi-tool.

Pro tip: Pack everything in waterproof dry bags or ziplock sacks. Rain showers can come quickly in the hills, and damp gear can ruin your day.

4. Access the Trailhead

The primary trailhead for Hickory Hill is located at the end of Hickory Hill Road, approximately 2.3 miles from the intersection with Route 22. There is a small, unpaved parking area that accommodates 8–10 vehicles. Arrive early on weekends—space fills quickly by 8:00 AM.

If you’re coming from New York City, take I-84 West to Exit 13 (Millbrook), then follow Route 22 North for 4.5 miles. Turn right onto Hickory Hill Road (look for the small brown trail sign) and follow it to the end. The road is narrow and winding—drive slowly, especially after rain.

There is no entrance fee, but donations to the Millbrook Land Trust are appreciated. A donation box is located near the trailhead kiosk.

5. Begin the Hike: The Loop Route

The Hickory Hill Trail is designed as a loop, and we recommend hiking it clockwise for optimal views and easier navigation.

Section 1: Trailhead to Creek Crossing (0.0–1.4 miles)

Start on a wide, well-maintained path lined with towering hickory, oak, and beech trees. The trail is gently ascending, with occasional roots and rocks to navigate. Watch for blue blazes painted on trees and rocks—these mark the route. After 0.8 miles, you’ll pass a small interpretive sign about the local flora and the history of the land, once used for small-scale farming in the 1800s.

At 1.4 miles, you’ll reach a wooden footbridge crossing a clear, rocky stream. This is a popular rest spot. Take a moment to refill water here if needed—this is the only reliable water source on the trail. Use a filter or purifier before drinking.

Section 2: Ascent to Summit (1.4–3.2 miles)

From the stream, the trail becomes significantly steeper. This is the most physically demanding section. The path narrows and winds upward over exposed bedrock. Use your hands for balance in places—this is not a technical climb, but it requires attention.

At 2.5 miles, you’ll pass a side trail marked with a faded red blaze—this leads to an abandoned stone foundation, a remnant of a 19th-century homestead. It’s worth a short detour if you have time.

At 3.2 miles, you’ll emerge onto the summit ridge. The trees thin out, and the view opens dramatically. The summit rock is a large, flat slab of quartzite—perfect for sitting, eating lunch, and taking photos. On a clear day, you can see the Catskill Mountains to the west and the Berkshires to the east.

Section 3: Descent and Return (3.2–4.7 miles)

From the summit, follow the blue blazes as the trail descends along the western ridge. This section is less steep but features loose gravel and scattered boulders. Stay on the trail to prevent erosion.

At 4.0 miles, you’ll re-enter the forest and pass a large white pine with a carved heart and initials—a local tradition. Continue straight; do not take any side paths.

The final 0.7 miles are mostly flat, winding gently back to the trailhead. You’ll pass a bench placed by a local conservation group in memory of a longtime trail volunteer. Sit for a moment, reflect, and thank the land for the experience.

6. Leave No Trace and Exit Safely

Before returning to your vehicle, take one final moment to survey your surroundings. Pick up any trash you may have brought in—even small wrappers or fruit peels. Pack out everything you pack in.

Check your clothing and boots for ticks. Remove any you find with fine-tipped tweezers, grasping as close to the skin as possible. Wash your hands and monitor for symptoms of Lyme disease over the next few weeks.

Take a photo at the trailhead sign to document your hike. Share it responsibly on social media—tag the Millbrook Land Trust and use

HickoryHillTrail to help promote conservation efforts.

Best Practices

Practice Leave No Trace Principles

The Hickory Hill Trail thrives because of the respect hikers show for its environment. Follow these seven Leave No Trace principles:

1. Plan ahead and prepare. Know the rules, weather, and terrain. Don’t improvise.
2. Travel and camp on durable surfaces. Stick to the trail. Avoid trampling vegetation, even if it seems easier to cut switchbacks.
3. Dispose of waste properly. Pack out all trash, including biodegradable items like apple cores and banana peels. They don’t decompose quickly in forest ecosystems.
4. Leave what you find. Do not pick flowers, carve trees, or collect rocks. These are part of the natural heritage.
5. Minimize campfire impact. Fires are prohibited on the trail. Use a stove if cooking.
6. Respect wildlife. Observe animals from a distance. Never feed them. Store food securely.
7. Be considerate of others. Yield to uphill hikers. Keep noise low. Let the forest speak for itself.

Stay Hydrated and Pace Yourself

Many hikers underestimate the physical demands of the Hickory Hill Trail. The 1,100-foot elevation gain over 2 miles is deceptive—it feels steeper than it looks. Take frequent breaks. Drink water every 20–30 minutes, even if you don’t feel thirsty. Dehydration can sneak up quickly, especially in humid conditions.

Use the “talk test” to gauge your pace: if you can’t speak in full sentences without gasping, you’re going too fast. Slow down. Enjoy the journey.

Check the Weather Daily

Weather in the Hudson Valley can change rapidly. Always check a reliable forecast the night before and again in the morning. Use the National Weather Service (weather.gov) for accurate, localized predictions. Avoid hiking during thunderstorms—rocky summits are lightning hazards. If lightning is within 10 miles, descend immediately.

Hike with a Buddy

While solo hiking is possible on Hickory Hill, it’s safer and more enjoyable with a partner. If you must hike alone, leave your itinerary with someone you trust—including your expected return time. Consider using a personal locator beacon (PLB) or satellite messenger like Garmin inReach for emergencies.

Respect Cultural and Historical Sites

Along the trail, you’ll encounter remnants of human history: stone walls, old foundations, and even a forgotten well. These are archaeological artifacts. Do not disturb them. They tell the story of the people who lived here long before the trail existed.

Support Local Conservation

The Hickory Hill Trail exists because of volunteer efforts and private land donations. Consider becoming a member of the Millbrook Land Trust or donating to their trail maintenance fund. Volunteers regularly organize clean-up days and trail marker replacements—participating is a meaningful way to give back.

Tools and Resources

Recommended Apps

• Gaia GPS: Offers detailed topographic maps, offline access, and user-generated trail notes. The Hickory Hill Trail is pre-loaded in the New York trail library.
• AllTrails: Provides recent trail reviews, photos, and difficulty ratings. Filter by “less crowded” to find quieter times.
• Meridian: A free, open-source app with U.S. Geological Survey maps and compass functionality. Ideal for low-tech navigation.

Recommended Gear

• Footwear: Salomon X Ultra 4 GTX or Merrell Moab 3
• Backpack: Osprey Talon 22 or Deuter Aircontact Lite 20
• Hydration: CamelBak Crux Reservoir (2L) or Nalgene bottle with carabiner
• Trekking Poles: Black Diamond Trail Ergo Cork or Komperdell C3 Carbon
• Water Filter: Sawyer Squeeze or LifeStraw Peak Squeeze
• Headlamp: Petzl Actik Core or Black Diamond Spot 400
• Insect Repellent: Repel Lemon Eucalyptus or Sawyer Picaridin
• First Aid Kit: Adventure Medical Kits Ultralight/Watertight .7

Books and Guides

• Hiking the Hudson Valley: 50 of the Best Day Hikes by Jim Mastro
• Trail Guide to the Catskills and Hudson Highlands by David M. Kelsey
• Leave No Trace: A Guide to the New Wilderness Ethics by The Leave No Trace Center for Outdoor Ethics

Online Resources

• Millbrook Land Trust Official Site – Trail maps, rules, volunteer opportunities
• National Park Service Hiking Guidelines – Universal best practices
• US Hiking – User-submitted trail reports and photos
• AllTrails Hickory Hill Trail Page – Real-time reviews and recent photos

Weather and Trail Conditions

• National Weather Service – New York / New Jersey
• AHM Rain Radar – Real-time precipitation tracking for the Hudson Valley
• Sign up for the Millbrook Land Trust email newsletter for trail closure alerts and seasonal updates.

Real Examples

Example 1: Sarah, 34, First-Time Hiker

Sarah had never hiked more than a mile before deciding to tackle Hickory Hill on a crisp October morning. She followed the gear checklist in this guide and brought a friend who had hiked the trail before. “I was nervous about the climb,” she says. “But the trail markers were clear, and we stopped every half-mile to rest. The view from the top made me cry. I didn’t know nature could feel so powerful.”

She posted her experience on Instagram with the hashtag

HickoryHillTrail, which led to her joining a local conservation group. She now volunteers monthly to help maintain the trail.

Example 2: James and Elena, Retired Hikers

James and Elena, both 68, hike Hickory Hill every fall. “We’ve been coming here for 17 years,” James says. “We bring our thermos of tea and sit on the summit rock for 20 minutes. We don’t rush. We listen to the wind in the leaves.”

They’ve witnessed changes: more visitors, more litter, and fewer wildflowers in recent years. “We pick up trash every time,” Elena adds. “It’s not hard. And it matters.”

Example 3: The Hiking Club from Poughkeepsie High

A group of 12 high school students from Poughkeepsie completed the trail as part of an environmental science project. They documented the trail’s biodiversity, collected data on invasive plant species, and presented their findings to the town council.

As a result, the school partnered with the Land Trust to create a student trail ambassador program. Now, each year, students help install new trail signs and lead guided hikes for younger children.

Example 4: The Winter Hiker

Mark, a 42-year-old outdoor photographer, hikes Hickory Hill in January to capture the frozen stream and snow-dusted summit. He uses microspikes and a DSLR with a telephoto lens. “The silence is unlike anything else,” he says. “You hear your own breath. And the light—when the sun hits the rocks just right—it’s like the mountain is glowing.”

His photos were featured in a regional nature magazine and helped raise awareness about winter hiking safety.

FAQs

Is the Hickory Hill Trail suitable for children?

Yes, but only for older children (ages 8 and up) with good stamina and experience on uneven terrain. The steep sections and rocky paths can be challenging for younger kids. Bring snacks, extra layers, and a carrier if needed. Many families complete the trail with a slow, playful pace—stopping to identify leaves, rocks, and birds.

Are dogs allowed on the trail?

Dogs are permitted but must be kept on a leash at all times. Owners are responsible for cleaning up after their pets. Some sections of the trail pass near sensitive wildlife habitats, so keeping dogs under control is essential for conservation.

Can I camp on or near the Hickory Hill Trail?

No. Camping is not permitted on the trail or within 200 feet of the trail corridor. The land is privately protected, and overnight stays are prohibited. Nearby options for camping include the Millbrook Woods Campground (12 miles away) or state parks like Fahnestock State Park.

Is there cell service on the trail?

Minimal to none. You may get a signal at the trailhead or on the summit, but not along most of the route. Assume you will be disconnected. Carry a physical map and compass.

How do I report trail damage or dangerous conditions?

Contact the Millbrook Land Trust directly via email at info@millbrooklandtrust.org or through their online reporting form. Include photos, location markers (GPS coordinates if possible), and a description of the issue. Volunteers respond within 48 hours.

What should I do if I get lost?

Stop immediately. Do not keep walking. Use your map and compass to reorient. If you’re still unsure, stay put. Use your whistle (three short blasts is the universal distress signal). If you have a satellite messenger, send your location. Emergency responders are trained to locate hikers using GPS data.

Is the trail accessible for people with mobility challenges?

No. The Hickory Hill Trail is not ADA-accessible. It features steep inclines, exposed roots, rocky steps, and uneven surfaces. There are no paved or graded sections. For accessible nature experiences in the area, consider the Millbrook Nature Preserve boardwalk loop.

Why are there so many blue blazes? Are they always accurate?

Blue blazes mark the main trail, but they can fade due to weather, moss growth, or vandalism. They are not always visible. Always carry a map and know your general direction. If you don’t see a blaze for more than 200 yards, stop and recheck your route.

Can I bike or bring a stroller on the trail?

No. The trail is designated for foot traffic only. Bicycles and strollers are prohibited to protect the ecosystem and ensure safety for all users.

How do I know if the trail is closed?

Check the Millbrook Land Trust website or their social media pages (Facebook and Instagram). Closures typically occur after heavy rain, ice storms, or during prescribed burns. Never enter a closed trail—signs are posted at the trailhead.

Conclusion

Hiking the Hickory Hill Trail is more than a physical activity—it’s an act of mindfulness, a tribute to the land, and a connection to something deeper than ourselves. The trail doesn’t demand perfection; it asks for presence. It asks you to slow down, to notice the way light filters through the canopy, to listen to the rustle of a deer in the underbrush, to feel the cool stone beneath your fingers as you climb.

By following the steps outlined in this guide, you’re not just preparing for a hike—you’re becoming a steward of this sacred space. Every step you take with care, every piece of trash you carry out, every rule you respect, contributes to the trail’s survival.

Whether you’re hiking alone at dawn, with family on a crisp autumn afternoon, or returning year after year like James and Elena, the Hickory Hill Trail will meet you where you are. It will challenge you, humble you, and reward you with quiet, enduring beauty.

So lace up your boots, pack your water, and step onto the trail. The forest is waiting.