A Senior Editor’s October: What Is Worth Your Time in the Hudson Valley This Month
By Mr. Brown
October in the Hudson Valley is not a secret. I want to say that plainly before saying anything else, because the column that begins with "escape the crowds and discover" is not the column I intend to write. This is a month when the valley earns its reputation honestly, when the light arrives at a lower angle and touches the ridgelines with more deliberation than it manages in any other season. That reputation draws precisely the kind of crowds that can make the wrong choice of destination feel like an obligation you should have declined. My job, as I see it, is the same here as it is on a page: cut what is merely popular, keep what is genuinely worth your time.
This October, four things meet that standard. I will tell you where I am going, and why each one earns the trip.
The Old Rhinebeck Aerodrome, Red Hook (Weekends through October 18)
The aerodrome in Red Hook does something I find difficult to explain quickly and easy to recommend completely. On weekends through October 18, it flies aircraft from the pioneer era of aviation and the First World War, off a grass runway in Dutchess County. After the 18th, the field goes quiet until next season. Our colleague Silas Van Wyck has written about it in "Last Flights of the Season at the Old Rhinebeck Aerodrome," and he finds the right register: this is a place where the twentieth century has not entirely settled in. These are not replicas. They are the original argument, the one made against common sense and gravity, that flight was possible at all. The collection is, by any honest measure, one of the finest of its kind in the country, and the fact that these machines are still flown rather than merely displayed is the point of being there.
I will be going on a weekend before the 18th. If you have never been, go before the season closes. If you have been before, go again. Some things improve on repetition, and watching a First World War biplane lift off a grass field on a clear October afternoon is one of them.
The New York State Sheep and Wool Festival, Rhinebeck (October 17 and 18)
The Sheep and Wool Festival arrives each year at the Dutchess County Fairgrounds in Rhinebeck on the third weekend of October, and it draws a specific kind of crowd: not a tourist crowd, but the kind that knows precisely what it has come for. Spinners, weavers, breeders, dyers, vendors of materials with long traditions and strong opinions about them. This is a working gathering, and that is what makes it interesting to someone who is not a weaver. The craft is the attraction, and craft at this level of seriousness carries its own energy.
Our companion piece, "Sheep, Wool, and Everything After: Rhinebeck's Biggest Autumn Weekend," covers the full scope of what to expect, and I recommend reading it before you go. I will add a logistical observation: October 17 and 18 are also the aerodrome's final weekend. A Saturday that begins in Red Hook and continues in Rhinebeck is a Saturday very well spent. The two venues are not far apart, and the combination asks something of you, a willingness to pay attention to things made by hand and by engine alike, that the valley rewards generously.
Sleepy Hollow, Westchester County (All Month)
Sleepy Hollow sits across the river in Westchester, which places it just outside the Hudson Valley's most common itinerary. That is precisely why I am including it. Our companion essay, "Sleepy Hollow: The Place That Wrote Its Own Legend," by Silas Van Wyck, takes the town seriously in a way that October coverage rarely does, and the seriousness is the correct approach.
The Old Dutch Church of Sleepy Hollow was founded around 1685, when this stretch of the valley was still a Dutch colonial venture a single generation removed from New Amsterdam. The burying ground beside the church holds stones that are worn and canted and largely illegible, which is, as Van Wyck observes, fitting. Washington Irving did not invent this place. He worked with what was already there. In October, Sleepy Hollow does lean into its legend, and some of that is commercial and some of it is not. The church and the churchyard are primary sources, not atmosphere. I would go on a quieter weekday if you can manage it, and I would go with Van Wyck's essay read beforehand.
NARA, via Wikimedia Commons (public domain)
Metro-North's Leaf Peeper Hudson Line Trains (Through November 8)
Metro-North is running additional Hudson Line trains through November 8. They are called, without irony, the Leaf Peeper trains, which is a cheerful name for a service that is genuinely useful. Our piece, "The Leaf Peeper Trains Are Coming: Metro-North Adds Hudson Line Trains Through November 8," has the schedule details. My suggestion is to use these trains not as a leaf-peeping delivery mechanism in the literal sense but as a reminder that the valley reads differently from a train window than from a car on Route 9 on a Saturday in foliage season. The Hudson sits beside you for long stretches. The light, on a clear October afternoon, makes the same argument I described in the first paragraph, and it makes it moving, which is to say in motion, which is to say the way arguments are best received.
What I Am Skipping, and Why
There are harvest festivals this month that I will not be covering, not because they lack charm but because they have become efficient at converting charm into commerce. I am also skipping the most photographed orchards, not because the apples are anything less than excellent but because the queue for the cider doughnuts is its own form of October penance. These are not recommendations against; they are simply not where my attention is going this month.
The test I apply each month is not how much there is to do but how well chosen it is. October in the Hudson Valley keeps passing that test, as long as you are the one doing the choosing.
Sources and Further Reading
• RFTUV: Sheep, Wool and Everything After: Rhinebeck's Biggest Autumn Weekend
• RFTUV: Last Flights of the Season at the Old Rhinebeck Aerodrome
• RFTUV: The Leaf Peeper Trains Are Coming: Metro-North Adds Hudson Line Trains Through November 8
• RFTUV: Sleepy Hollow: The Place That Wrote Its Own Legend
Tony Webster, via Wikimedia Commons (CC BY-SA 2.0)

