Every September, two rituals mark the start of fall in Richmond. You drive out Swamp Road to Bartlett's Orchard for the first bag of Paula Reds, and at some point before the leaves peak you make the climb up Perry's Peak Road to Hollow Fields for the view off Yokun Ridge. They feel like the same kind of tradition, weather-dependent, seasonal, the sort of thing you do without thinking too hard about it.
They are not the same kind of tradition. One runs on a clock that resets every single year no matter what happened the year before. The other has been stuck on the same "temporary" setting for years, and it will not move until a land access question gets settled, not until the calendar flips to October.
If you only check one of these before you head out, you're checking the wrong one.
The orchard's clock always resets
Bartlett's Orchard has been on Lenox Mountain since 1947, and the Bartlett family is now four generations into growing apples on the same 52 acres. The rhythm is simple and public: pick-your-own opens Labor Day weekend and runs through Columbus Day weekend, with the farm sometimes staying open later depending on how the crop is holding up that particular year. Paula Red comes first, then Jonamac and McIntosh, working through a lineup that eventually includes Cortland, Gala, Macoun, Empire and a half dozen others before the season closes.
That "depending on the crop" clause is not boilerplate. Three years ago, a hard frost on the night of May 18 hit apple blossoms across Berkshire County while they were at their most vulnerable, and Bartlett's lost most of that year's crop before it ever set. Cold air sinks, so trees at the bottom of the 200-foot elevation change on the property came out worse than the ones near the top. Rick Bartlett, who runs the orchard with his brother Ron, canceled pick-your-own that fall and told customers on Facebook, "we look forward to much better weather and a normal crop next year." Jaeschke's in Adams and Lakeview Orchard in Lanesborough made the same call that season for the same reason.
The point isn't that one bad spring happened. It's that an orchard's season is a fresh roll of the dice every single year. A frost, a wet bloom, a good crop, it all gets tallied up and settled by October, and then next May the count starts completely over. Nothing carries forward. If this year's blossoms came through clean, you'd have no way of knowing that from what happened three Mays ago, and neither would Bartlett's. That's exactly why the orchard's website hedges its own season dates rather than posting them as fixed: the clock resets, but nobody knows what it's going to hand you until the trees tell you.
The trail's clock doesn't reset at all
Perry's Peak Loop sits inside Hollow Fields, a 660-plus acre reserve of hayfields and forest managed by the Berkshire Natural Resources Council off Perry's Peak Road. The full loop is about 3.7 miles round trip with a steep climb through oak, beech and stands of red pine, and it passes Richmond Overlook, known locally as Scotty's Lookout, on the way to the forested summit. The shorter Fields Trail, about 2 miles round trip, gets you a bench and a clean view of Yokun Ridge without the elevation gain.
Here's the part that doesn't behave like a season. A section of the Perry's Peak Loop crosses onto Richmond Town Land, and public access there was rescinded by a neighboring private landowner. BNRC's own reserve page still describes this as temporary, with efforts underway to relocate the trail and restore full access. That language isn't new this year. It has carried across BNRC's site, hiking apps, and trip reports going back well before this season, which tells you something an app can't: this isn't a seasonal closure that lifts with better weather or a drier trail. It's a property line problem, and property line problems get solved through negotiation and legal process, not by the arrival of October.
Practically, that means the full loop is currently an out-and-back rather than a circuit. Hikers climb the west side of the loop to reach Richmond Overlook and the summit, then retrace their steps back down instead of continuing around. The Fields Trail and the lower meadows are unaffected, since the closure only applies to the section where the loop crosses onto town land. If the west-side trailhead on Perry's Peak Road looks crowded or the gravel road is rutted from mud, Bates Memorial State Park in Hancock is the other approach BNRC lists to reach the same peak.
What actually changes week to week
The two clocks intersect in one useful place: reserve hours. BNRC runs Hollow Fields on a seasonal schedule that shifts as daylight changes, while Bartlett's farm store holds the same hours year-round and only adds the pick-your-own window on top.
| Hollow Fields Reserve | Bartlett's Orchard Farm Store | |
|---|---|---|
| Fall (Sept-Oct) | 7 a.m. to 7 p.m., gate closes automatically | Weekdays 7 a.m. to 5 p.m., weekends 8 a.m. to 5 p.m., plus pick-your-own after Labor Day |
| Summer (May-Aug) | 6 a.m. to 8 p.m. | Same store hours year-round |
| Winter (Nov-Feb) | 8 a.m. to 5 p.m. | Same store hours year-round |
| Spring (Mar-Apr) | 7 a.m. to 7 p.m., road can turn to deep mud | Same store hours year-round |
Notice what doesn't shift: Bartlett's store hours are flat across all four seasons, because the farm store is a retail operation and retail hours don't care what the trees are doing. What shifts at Bartlett's is the pick-your-own window layered on top, which is entirely weather-triggered. Hollow Fields is the reverse. Its official hours change with daylight and season like clockwork, twelve months a year, completely unrelated to the trail closure, which has nothing to do with daylight at all and everything to do with who owns the parcel the trail crosses.
That's the distinction worth carrying into the next six weeks. A closed pick-your-own season at Bartlett's is a one-year event with a known cause and a known reset date: next May. A closed trail section at Hollow Fields is an open-ended situation that will resolve on its own timeline, whenever the relocation effort BNRC describes actually gets built and approved. Checking "is the orchard picking yet" and checking "is the trail open" are two different kinds of question, even though they show up in the same September search bar.
Small towns keep two kinds of records
Richmond doesn't have a town square with a bulletin board that tracks both of these, so the knowledge lives in whoever's been paying attention. Longtime residents already route around the Perry's Peak closure without thinking about it, the same way they already know to call ahead in a rough apple year instead of driving out to Swamp Road on a hunch. Neither habit shows up on a map app until you're standing in front of a locked gate or an empty row of trees.
That kind of local pattern recognition, knowing which changes are seasonal and which ones are structural, is the same instinct that matters when you're trying to understand anything else about a small town like Richmond, whether it's a trail, a tax rate, or a piece of property. Diane Thorson has spent years working in these towns and tracking exactly these kinds of details, the ones that don't show up until you've actually lived with them for a while. If you're ever curious what else is worth knowing about Richmond, or any of the towns around it, reach out and schedule a consultation.
