Cross-Country Skiing Adventures

A plethora of trails throughout Prospect Mountain takes cross country skiers through a serene wilderness.

We were coming back from a walk on Mother’s Day last year in Brattleboro, on the street where Jen’s son, his wife, Lauren, and baby Greta Jean live. It had been a wonderful, warm spring walk replete with trout lilies and spring beauties. As we descended out of the woods, Jen started chatting with some of her old neighbors.

“David,” she called me over, “you won’t believe what Jack did this morning.” I turned, and Jack said, “I was skiing at Prospect, the conditions were fantastic.” On a warm, spring morning, in May. I was so jealous. This is by way of illustrating that Prospect has snow when most other cross country ski areas are thin, scratchy and melted away. That’s because the base is at 2,250 feet and the summit is 500 feet higher. When it’s 35 degrees and raining or sleeting in Keene or Brattleboro, it’s snowing at Prospect.

Prospect is one of the first places we ski in December and one of the last in April. And the grooming is always excellent. Yes, it’s a long haul, especially from Keene to Woodford on Route 9, just before the long hill down into Bennington, but it’s worth it. (Though I am always hesitant to drive Route 9 when it’s snowing. Memories of a full 360 degrees on a snowy morning in my old Saab 96).

But on sunny days it’s glorious, and the Green Mountain wilderness is palpably wild. The ski area feels wild as well, a glimpse back into the unfancy skiing of yesteryear. Prospect was a downhill ski area until it closed in the early 1970s. After languishing for a while, it was reopened as a Nordic area. The old downhill slopes are kept open and are great for backcountry skinning and skiing. And now there’s a lavish network of cross-country trails sprawling out to the west and east from the base. The lodge is like stepping back into a 1950s ski museum. Funky log picnic tables, a fireplace, low ceiling, smell of wet wool, a cozy little snack bar — exactly where you wouldn’t want to be in a pandemic and exactly where you want to be when this COVID-19 mess has abated some. It’s the home to the Williams College Nordic Team, so there’s always a buzz, and young, vibrant skiers in flashy outfits skate-skiing by the rest of us crunchy old Nordorks.

There are four separate little worlds at Prospect. World #1 is the complex network of wide, mostly mellow trails to the west of the lodge. World #2: the Alpine touring trails of the old ski area. Too steep for those of us without backcountry gear. In World #3, the trails narrow, and somewhat steep trails that climb up to the summit on the east side of the old ski area mountain and then twist and turn back down to World #1 on the west side. It’s a longish climb up and a fast ride down. Challenging, but not scary.

Disappointingly, there’s not a mondo view after the long climb, but it’s still worth it. And after years of skiing at Prospect, we just discovered World #4 to the east of the lodge, where there’s an interesting network of wide trails that weave in and around the Greenwood Lodge and Campsites — lots of ponds, meadows and interesting loops. Great for sunset viewing at the end of an afternoon. Here’s a nice 90-minute, 8K loop around the perimeter of World #1. This will sound complicated, but essentially, you’re just skiing the outside edge of all these west-side trails.

Leave the lodge area climbing gently onto Woodpecker Trail. Then successively turn right onto EZ Way, Troll Road, Christmas Tree, Beaver Pond, Duke’s Loop, Chickadee, Duke’s Loop and Catamount. From the next intersection, head straight ahead onto Workout. Then take a left back onto Troll Road and follow it to Woodpecker, then back to the lodge.

A couple of notes:

At the bottom of the hill on Beaver Pond, follow a little side trail out onto the frozen pond for a pristine Vermont wilderness experience. Follow the pond shore to the left (or gallivant around on the open pond) until you find another slightly scrappy side trail to connect you back up to Beaver Pond Trail.

Chickadee is the only black diamond trail on this loop, but it’s not that hard. There’s a slightly long, steep climb in the beginning but then it bends around and descends pleasantly back to Duke’s Loop. If you don’t want the strenuousness of the climb, just stay on Duke’s Loop. If you get back to the lodge and want to ski a bit more, head over to the Greenwood Acres area for some pleasant poking about.

I’ve skied at Prospect probably a dozen times in the past five years and I like that I can keep discovering new corners. The snow is really dependable and the gigantic windmills in Searsburg that loom over Route 9 are always an impressive site.


If you need to warm up afterwards, consider stopping in at the Woodford General Store across Route 9 from the entrance. There are always a couple of hot soups on offer. It has the same backwoods Vermont feel as the lodge and is one of the few new things in Woodford since I lived there during the winter of 1971-72. I love the sign in the eaves that proclaims: “Woodford City, population 414.”

If you want to drive a bit to stop for a late lunch, consider the Village Roost in Wilmington for eat-in or take-out. It’s an intriguing menu with things like Poutine, Vietnamese Lemongrass Beef Roll and excellent Falafel. There’s also a rustic, chic bar upstairs at the Cask and Kiln, located right at the light in downtown Wilmington. This was a regular stop for us pre-pandemic, in part because of the exotic Russian bartender.

A bit further along you could stop at Beer Naked and Pizza Palooza at the Hogback Summit in Marlboro. We’ve heard that it’s one of the best post-ski pizza places in Vermont. And the locally brewed ales get good reviews too. You certainly can’t beat the views. We’re waiting until post pandemic, or both of us are vaccinated, to try out this kind of venue.