Published August 13, 2026 10:16AM
I wanted to plant a seed with my daughters: that running, including the more competitive, pin-on-your-bib variety, is as much about traveling somewhere new as it is about discovering something about yourself. Outdoor people have a taxonomy for this. Type 1 fun is fun while it’s happening: ice cream, a pool, a chairlift. Type 2 fun is miserable in the moment and fun later, in the reflection of what you just went through (and usually includes musings of when you’ll get to do it next). Type 3 fun is not fun at any point and sometimes ends in a helicopter rescue. I think the trick to maximizing fun isn’t avoiding Type 2—if you’re healthy enough for it, you gotta keep Type 2ing. The trick is keeping the portion small and surrounding it with enough Type 1 to cushion it. Getting outdoors doesn’t have to be an all-in pursuit. And if you’re agro enough to think that, I guess you can call everything that’s not your Type 2 pursuit “recovery.”
I chose the Litchfield Hills Road Race (LHRR) as the setting for this life lesson. Litchfield is a little Connecticut town (population about 1,250) two or three hours from New York, depending on traffic. My trips out of the city and into nature have lately centered on the Catskills, and Litchfield feels like a different country—more New England, more pressed. Agrarian but refined. Less Catskills, more Cotswolds.
The race distances were manageable: a 7-miler for me, a 2.3-mile race for my 13-year old daughter, who runs cross-country and has opinions about Hokas, and a one-mile run for my 10-year old daughter—her first race ever. The cannon (it’s a literal cannon) doesn’t fire until 1 P.M., which the race’s own website frames as a perk: “Sleep in.” This is true. It is also true that a June race starting at 1 P.M. is the exact moment the sun absolutely sucks. This leads to a nickname for part of the race: “Microwave Mile”—an unshaded stretch along Whites Woods Road, appropriately near St. Anthony Cemetery.
But the real reason I picked Litchfield was Belden House, which meant the Type 1 was handled before we ever pinned on a bib. Belden House & Mews opened last year in the center of town, a three-acre spread combining an 1888 Victorian mansion and a 1959 modernist annex—the town was a mid-century haunt of Marcel Breuer and Eliot Noyes. There’s a nice little pool and a spa, and the rooms are relaxing and distinct without being fussy or stupid-modern. But it’s arguably the food that makes the place. We drove up Friday in time for dinner: a seafood tower my daughters treated as an architectural excavation—poached shrimp, lobster ceviche, mussels in a green curry dressing—and then the aged duck breast, the standout, which is really duck three ways: croquettes, a broth with cappelletti, and the breast itself, served with fresh and charred ramps. Afterward the common room filled up—guests with their dogs, amaro and martinis, and a couple playing chess.
Saturday was the Type 1 clinic. We did easy, flat walks at Topsmead State Forest—a former estate with an English cottage sitting in a meadow—and around the White Memorial Conservation Center. We got fried artichoke sandwiches at Petraroia Deli on West Street, where I had my first Foxon Park White Birch Beer, a cane-sugar soda made in East Haven since 1922 and the kind of hyper-local specialty that makes a place feel like a place. We stopped for cream at Arethusa Farm (get the Almond with Toasted Coconut). At no point did anyone suffer.
Sunday, the races. The LHRR is a small-town production in the best sense—everything radiates from the Green, and the crowd support is completely out of proportion to the field. My younger daughter ran her mile through the streets around the town center. My older daughter did the best of all of us: eighth-fastest girl in the 2.3, on a course that includes a stretch of Gallows Lane—the hill Runner’s World has ranked among the ten most daunting in American racing. I did not tell her about the hill’s reputation until after.
My 7 miles were a mix of roads and hills, but also trails and grass, which gives the whole thing a very New England feel. For a little race, it’s pretty exciting. There are bands along the course, mostly classic rock, at least this year. My favorite moment: a band playing Tom Petty’s “Last Dance with Mary Jane” while a whiff of weed drifted over from what I assume was a spectator. Maybe another runner. That’s cool. Somewhere on Gallows Lane I brushed up against Type 3’s outer suburbs and adjusted my pace accordingly. There’s no shame in walking up Gallows Lane.
I don’t know what my daughters will remember about Litchfield. The duck, maybe. A medal in a drawer. A walk in the meadow. That’s all fine. I was never trying to convince them that racing is fun. They’ll need to find that in their own way. I was trying to show them that the hard part can be small, and everything around it can be easy. If that’s what stuck, I’m calling it a win. And if someday one of them wants to run the full seven? Well, I know a hill I won’t tell her about until after.
The Guide
Belden House & Mews
The hotel is new, but the pedigree isn’t: it’s a sister property to Troutbeck, the acclaimed Hudson Valley estate hotel in Amenia, and it’s already picked up a Michelin Key of its own. The complex today spans three buildings: the mansion, the 1959 modernist Mews out back, and the 1891 firehouse next door, a National Historic Landmark now repurposed as a meeting and event space. During the renovation, workers found the original 19th-century craftsmen’s signatures hidden in the woodwork. Some have been reproduced on the walls of select rooms. There’s a fifty-foot heated pool, the Bathhouse spa, and a lawn set up for croquet. The race itself runs the second Sunday in June, cannon at 1 p.m. sharp—book Belden well ahead, since the whole town fills up, and it’s close enough to the Green to walk to the start and skip the parking scramble.
Arethusa Farm
The ice cream shop is technically in Bantam, a few minutes south of the Green, and worth the short drive. Sixteen percent butterfat, made from the farm’s own herd. Get the Almond with Toasted Coconut.
Petraroia Deli
Sandwiches on West Street, on bread from The BakeHouse, Litchfield’s own scratch bakery. Get a Foxon Park White Birch Beer alongside — a cane-sugar soda made in East Haven since 1922 that you won’t find much outside Connecticut.
White Memorial Conservation Center
4,000 acres of trails, but the Little Pond boardwalk is the move with kids: flat, elevated above the marsh, about a mile and a half, and it crosses the Bantam River twice.
Topsmead State Forest
The former summer estate of Edith Morton Chase, who left it to the state in 1972 — flat meadow walks around an English-style cottage. The Cotswolds comparison, made literal.
