Within twenty minutes of this door there is more good walking than most people manage in a year.
That is a function of geology rather than luck. You are in the New Jersey Highlands, a band of old hard hills that never got farmed flat, so the wild country starts where the road ends instead of an hour further on.
Five below, in the order we would send you to them rather than in order of effort. The first two involve scrambling on rock, so boots rather than sneakers for those. And the thing nobody tells you first: parking is the constraint here, not the walking. The lots are small and they fill early at weekends.
1 · Surprise Lake and the Bearfort Ridge
The biggest climb of the five, and still the one to walk first. Abram S. Hewitt is the wild, undeveloped state forest immediately north of the house — no road runs through it, so it is reached on foot or not at all — and the ridge opens out over Greenwood Lake again and again before dropping to Surprise Lake, which is about as good as the name promises.
The rock underfoot is Bearfort puddingstone, a conglomerate that reads almost purple in certain light. Loops run from roughly four miles to eight depending on how much ridge you take on, and it is free.
Parking is the real constraint: small pullouts on the Warwick Turnpike, or the shared lot at the Greenwood Lake Marina for the State Line Trail, which holds a dozen or so cars and fills early at weekends. For the trophy, the State Line Trail meets the Appalachian Trail at the border, and a short push north reaches Prospect Rock — the highest point the AT reaches in the state of New York.
2 · Terrace Pond, Wawayanda
A cliff-ringed glacial pond tucked into the same Bearfort ridge, sitting in the rock like something deliberately placed. It is one of the true gems of the Highlands.
There is real rock scrambling on parts of the loop. Wear boots rather than sneakers, take more water than feels necessary, and do not attempt it in the wet unless you already know the route.
3 · Long Pond Ironworks
Flat trails through a preserved eighteenth-century ironworks village along the river. You are walking through the remains of an industry that once fed the whole region, and the ruins sit close enough to the path to read properly.
This is the best of the five with young children, and the best in poor weather, because nothing here depends on a view.
4 · Wawayanda State Park
Miles of well-kept trail, a swimming lake, and a stretch of the Appalachian Trail running through it. The great virtue of Wawayanda is that you pick your distance on the day and it is difficult to go badly wrong.
In high summer, combine a short walk with the swimming lake and call it a day well spent.
5 · Ringwood State Park
Waterfalls, lakes, and the manicured grounds of the New Jersey Botanical Garden at Skylands next door. The contrast is the appeal: rough woodland walking, then formal gardens, inside the same hour, which is not a combination this part of the country offers often.
Bare Rock is closed, and has been since 2024
If you have read elsewhere about Sterling Forest’s Bare Rock Overlook, know this before you drive over. The Bare Rock Trail west of the West Valley Trail, including the Vista Point itself, has been closed since the Jennings Creek fire burned through in November 2024 — the largest wildfire New York had seen since 2008 — and it remains closed while the ground regenerates.
The Bare Rock closure is not the only one. The park’s notice also shuts stretches of the Fire Tower, Lake to Lake, Sterling Ridge and West Valley trails. The rest of the park is open and well worth your time. We will put the vista back on this list when the park puts it back on theirs.
Two of these will not take your dog
All five take a leashed dog on the trails — New Jersey wants the lead six feet or shorter, and so does New York at Sterling Forest. But two exceptions are worth knowing before you drive out, because both are places this piece otherwise sends you.
Dogs are barred from Wawayanda’s swimming beach and from the water there, under a statewide rule covering every bathing beach in New Jersey. And they are barred from the botanical garden at Skylands, gardens being separately named in the same regulation. The trails around both are fine.
The Bearfort scrambles are the other thing to think about. Sections of that first walk involve hauling yourself up bare rock, and a dog that is happy on a woodland path may not be happy there — or may be happy going up and stuck coming down.
Out of season, all of this is free
Abram S. Hewitt and Long Pond Ironworks cost nothing at any time of year, which covers the first and third walks here. Wawayanda and Ringwood charge per vehicle, but only between Memorial Day weekend and Labor Day.
So an autumn or winter walk costs nothing anywhere on this page. Sterling Forest, over the line in New York, is on the state’s own list of parks you can visit free of charge; if you are making a habit of the New York parks that do charge, the Empire Pass pays for itself in about eight visits.
Take the layer you think you will not need
Highlands weather is genuinely changeable and the ridges are colder and windier than the lake, by more than the distance suggests. Signal is good but not uniform, so download the map before you leave the house rather than at the trailhead, where you may not be able to.
None of these is a day out. That is the point of them: ninety minutes on the ridge and you are back before the house is awake, with the lake looking different for the rest of the weekend because you have now seen it from above.