The small gravel lot behind Mackey's on Route 66 holds about eight cars on a good day. It fills early on cool mornings, cars angled in without much order, tailgates open while people swap water bottles and leash up dogs. Nobody parks there because Mackey's sells trail maps. They park there because the pet supply and garden center sits a few steps from a break in the trees where the Hop River Trail crosses the road, and because everyone in town has quietly figured out the same thing: this stretch of old rail bed is no longer just a place to walk the dog. It has become the fastest way to string together a Saturday.
Most write-ups about small Connecticut towns treat their attractions like pins on separate maps. The winery gets one paragraph. The farm stand gets another. The lake gets its own section entirely, as if a resident drives to each one independently, parks, does the thing, and drives home. That framing misses what's actually happening in Columbia this fall. The Hop River Trail runs directly past or within a short walk of the town's working farm store, its hillside winery, and a town-owned preserve, which means the "list of things to do" is really one continuous corridor. You don't choose between them. You move through them.
The Trail Is the Point, Not the Backdrop
The Hop River State Park Trail follows a former rail line for more than 20 miles through Manchester, Vernon, Bolton, Coventry, Andover, and Columbia, a crushed-stone path that trades pavement for tree cover and the occasional stone rock cut. In Columbia specifically, the trail runs remote and quiet, crossing fields and following the river itself rather than winding through subdivisions the way it does further west. At its eastern end, it connects to the Air Line Trail and the East Coast Greenway, the long-distance path that in theory runs from Key West to the Canadian border. Nobody in Columbia is walking to Florida this weekend. But the practical version of that fact matters: the trail through town is part of a maintained, marked system with real access points, not an informal path that dead-ends at a fence.
Those access points are where the loop actually starts to make sense. Parking is limited and scattered on purpose, since this is a rail-trail through a town of open space and working farms, not a park with a visitor center. That means where you park decides which half of the loop you see first.
| Access Point | What's Within Reach |
|---|---|
| Small lot behind Mackey's, Route 66 | East Willow Farm's store, a short walk down Route 66 |
| Parker Bridge Road crossing | Quiet river-side stretch, pond views, closest to Heartstone's hillside vineyard |
| Lake Road | Columbia Lake and its public access, roughly at the trail's midpoint through town |
None of these lots are large. That's the town's character showing through its infrastructure. Columbia hasn't built a destination trailhead with a paved lot and a kiosk, because the trail was never meant to be a destination on its own. It was meant to connect places that already existed.
Cider Season at Two Ends of the Same Walk
East Willow Farm runs its store at 402 Route 66, close enough to the Mackey's lot that walking there and back barely counts as a detour. It's a working farm operation rather than a seasonal pop-up, stocking produce and meat alongside honey, maple syrup, and rotating stock like fresh-bottled raw milk and baked goods depending on the week. Fall is when the shelves shift toward cider-season staples, the kind of stop that makes sense on the way out on a loop, before the legs are tired and before the cooler in the trunk gets warm.
Heartstone Farm & Winery sits at the other end of the practical loop, at 468 Route 87, on 56 acres that climb to about 600 feet, one of the higher points in Columbia. The winery planted six cold-hardy grape varietals on land the family added to their existing berry and grass-fed beef operation back in 2008, and the patio looks out over the vineyard rows rather than a parking lot. Heartstone hosts food trucks and live music on a regular schedule through the season, which means the same rail bed that gets you to a farm store for cider ingredients also gets you to a place to sit down with a glass of something made from grapes grown on that same hillside.
The distance between the two isn't something either business advertises as a matched pair. But the trail makes the connection real in a way that driving between them on Route 87 and Route 66 never quite does. In a car, East Willow Farm and Heartstone Winery are two unrelated stops on two different roads. On foot or by bike, they're the two bookends of the same walk.
Szegda Farm Fills the Middle Mile
Between the farm store and the winery, the loop has a quiet middle stretch that most visitors from outside Columbia never find: the Szegda Farm trails. The town acquired the property in 2008 using Columbia's own open space fund alongside a state DEEP grant, with the specific goal of keeping the land in agricultural use rather than converting it into a conventional park. The result is 1.8 miles of hiking trails split across an upper and lower section, connected by an unmarked mown path through an open field, with two small separate parking areas on Szegda Road for each half.
This is the part of the loop that never shows up in a generic roundup, because it isn't a business with a sign or a website. It's town-owned land that happens to sit exactly where a walker or rider would want a break between errands, a stretch of open field and second-growth woods that turns a farm-to-winery walk into something closer to a real hike. The fact that it exists at all, preserved specifically to stay agricultural rather than manicured, says something about how the town has approached its open land generally: less interested in building a single flagship park, more interested in keeping working and semi-wild land connected to everything around it.
Where the Lake Fits When the Vines Go Quiet
Columbia Lake sits roughly at the midpoint of the trail's run through town, reachable from the Lake Road access point. It's the town's most popular single attraction by a wide margin, filling with swimmers, kayakers, and anglers through the warm months. The Columbia Lake Association has organized around it since 1935, back when membership was limited to lakefront property owners and social life meant square dances and potluck suppers. The association's mission has since broadened to include the whole town, and it still centers on the same idea it started with: the lake as the place where Columbia gathers.
As the weather turns and Heartstone's patio season winds down, the lake becomes the cold-weather alternative stop on the loop rather than the warm-weather one. The water views replace the vineyard views. The walk changes character without changing its basic shape: park near a trail access point, walk a stretch of the same rail bed, end up somewhere that gives you a reason to have made the trip.
One Season, One Loop
The easy version of a Columbia guide lists a winery, a farm stand, a lake, and a trail as four separate entries and calls it a day. The more accurate picture is that three of those four are strung along the fourth, and the fourth is what turns a handful of scattered errands into an actual weekend. That's not a coincidence of geography. It's what happens when a small town keeps its open space connected instead of parceled off, and it's worth knowing if you live here and have been treating Mackey's lot as just a place to park for a walk, rather than the start of a loop that ends with a glass of wine on a hillside or a walk along the water, depending on which way the season is turning.
If you're weighing a move to Columbia, or you already live here and are curious what your property is worth in a town where the land itself does a lot of the work, Cindy Muska has spent years walking these same roads with buyers and sellers. Reach out for a free home valuation and a conversation about what's actually happening on your street, not just on the map.
