Considering it is relatively close to Boston, we believe Mount Monadnock offers the best trek opportunities in New England—summits in the White Mountains are farther away, and require longer climbs before emerging above timberline. On the contrary, climbing the Monadnock, you will quickly leave the woods to be faced with steep rocks, hike in a desert-like environment, where only a few twisted trees fight the wind and cold, and have the possibility to walk along the ridge for a while, with nothing but air on both sides. Overall, there are 40 miles of hiking trails across the Monadnock State Park.

We call this trek the Big One because it is just about the longest route you can find on the Monadnock and still make it in a day. It also takes you away from the trade route up to the summit, and you should not meet too many people, even In summer.

Leave your car at the Old Toll Road trailhead and parking lot. A Ranger at the small gatehouse will collect the $3 entrance fee and hand you a map of the trail network.

Walk past the gate (toilets nearby) up the Old Toll Road. When you reach a clearing called the Halfway House site, continue straight and follow the signs for the White Arrow Trail, that you will follow up to the summit. When you emerge above timberline, the trail can be harder to follow. When you arrive at a mark, be careful to see the next white blaze on the rocks before you proceed, or you may get lost. The trail becomes steeper before you reach a small col just under the summit.

From there, you will follow the Pumpelly Trail along the ridge for a while – again, take your time to spot the marks before you leave the summit – look for them in the general direction of the ridge in the northeast. Once on the ridge, you may feel far away from New Hampshire, and closer to some landscapes of Southern Europe, with short vegetation and rocks everywhere. After about 1.5 miles, take the Cascade Link to your right and hike down to the White Dot Trail. Take the White Dot Trail to your left to the Park headquarters, campground and visitor center. Walk past the parking lot and take the Parker Trail at the far end of the lot. In about 1.5 miles, it will bring you back to the Old Toll Road. Take the Road on your left to walk back to your car, about 0.6 mi away.

Allow at least 7 hours to make the Big One trek, and more if you are walking slowly and plan to stop at the summit for a while. If you would prefer a shorter hike that still takes you to the summit and through most of the same wild scenery, go for our Direct Route to Mount Monadnock.

Remember that weather can be nasty at the summit while perfectly fine at the parking lot. We recently had our map literally shredded by rain and wind after 20 minutes on top of the mountain. Always check the weather before leaving, and be prepared to turn back if you feel cold or uncomfortable. Rocks can be slippery in rainy weather along the whole route - be extremely cautious when ascending and descending both in open spaces and in the woods. Finally, be aware that accidents often happen on the way back, when fatigue kicks in. Always stay focused on what you’re doing, and stop frequently to rest if you feel tired.

Finally, never leave without the map handed out by the Ranger at the gatehouse. If you are not comfortable reading a map, attend an orienteering class.