The Berkshires hold a concentration of golf courses that is unusual for a rural county of its size, and the reason is the same one that explains its museums: a century of summer residents with money, building the things they wanted nearby.
What distinguishes golf here is the terrain. These are hill-country courses, laid over ground that was never flat, and several of them are attached to former estates. The result is a set of courses with more elevation change and more awkward lies than a visitor from flatter country expects.
Why spring and autumn are the best of it
High summer is when most visitors come, and it is not when the golf is best.
July and August in the Berkshires bring humidity, afternoon thunderstorms and the county's peak visitor numbers. Courses are busier, tee times are harder to arrange at a convenient hour, and the pace of play slows.
Spring and autumn are quieter, cooler and drier. Tee times can generally be had at short notice and at reasonable hours, and a round moves at a pace set by the players rather than by the group ahead. Autumn adds the foliage, which for anyone who has not played a New England course in October is worth the trip on its own.
The trade-off is season length. Courses here open later and close earlier than those an hour south, because the ground stays cold. A mild April is not a guarantee of an open course, and the first frost ends things sooner than in the valley.
What hill terrain does to a round
Three things, all of which catch out visitors playing a Berkshire course for the first time.
Uphill and downhill lies are constant. Fairways cut into a hillside rarely give a flat stance, and the ball is above or below the feet far more often than on a flat course. Club selection has to account for it, and most visitors under-club uphill for the first several holes.
Elevation change alters distance more than expected. A tee shot dropping forty feet flies considerably further than the same shot on the flat, and one climbing the same amount falls short. On courses with several such holes this compounds across a round.
Wind behaves oddly. Hills channel and shelter, so the wind at the tee frequently bears no relation to the wind at the green. Reading it from the flag rather than from the feel at address is the habit to acquire.
Anyone playing here for the first time should expect to score worse than usual and should not read anything into it.
Choosing a course
The county's courses range from private club layouts attached to resorts and estates to modest public courses that will take a visitor on the day. The distinction matters, because the private end requires arrangement in advance and the public end frequently does not.
Resort courses are the easiest to arrange for a visitor staying nearby, and are usually the most expensive. Municipal and semi-private courses cost a fraction of that and are perfectly good golf on interesting ground.
Anyone travelling specifically to play should establish access before booking accommodation rather than after. Where to stay is covered on area lodging.
Golf as part of a Berkshire trip
Golf sits awkwardly in a Berkshire itinerary, because a round takes most of a day and the county's other attractions are concentrated in the same hours.
The arrangement that works is to play early and use the afternoon for everything else. Morning tee times are readily available outside high summer, and an eleven o'clock finish leaves the afternoon free for the museums and performances that are the county's larger draw — see cultural attractions and about the Berkshires.
For a group where not everyone plays, the county is unusually accommodating. The non-golfers have an entire cultural season within half an hour's drive, which is not true of most golf destinations. Group arrangements more broadly are on group rates.
Other warm-weather options
For anyone who finds a full round more golf than they want, the county has the usual range of shorter formats, and a great deal of outdoor activity that is not golf at all — walking, covered on hiking, water on on the water, and the summer operation on the ski hills on summer.