You Don’t Have to Know a Damn Thing About Horses to Have a Great Day at Highlands
Sponsored by Highlands Hudson Valley.
If the phrase “CSI5*” makes you think crime procedural, congratulations: this guide is for you.
Highlands Cup Week runs Oct. 7–11 in Amenia, and yes, some of the best riders and horses in the world will be there. But the part most people miss is that you do not have to be a horse person — and you definitely do not have to spend $400 — to have a very good day here.
Across the week, Highlands layers international show jumping with local food, shopping, family activities, contemporary art, hospitality and a Sunday car show that puts rare automobiles and motorcycles on the same estate as a $340,000 Grand Prix.
So instead of asking, “Do I like horse shows?” the more useful question is: “Which version of Highlands sounds fun to me?”
First: you do not have to buy a $400 ticket
General admission is free. Your free ticket gets you competition viewing, with additional food, shopping, family activities and event experiences available across Highlands Cup Week.
If you want a small upgrade without turning the day into a luxury splurge, the Fan Zone is $35 and includes covered ringside views, picnic-table seating, easy access to Vendor Village and one drink ticket.
That matters because Highlands can look expensive from the outside. The actual entry point is much friendlier.
Highlands spans a 1,000-acre estate in Amenia. Photo courtesy of Highlands Hudson Valley.
What are you actually watching?
The short version: horse and rider take on a course of jumps. Rails down and refusals can add faults; time matters; and the cleanest, fastest rounds rise to the top. You do not need to memorize any of that before you arrive.
Saturday, Oct. 10 at 4 PM is the $200,000 Mission Foods Racing Major League Show Jumping Team Class. The team format adds speed, strategy and a very obvious scoreboard — probably the easiest marquee class for a first-timer to follow.
Sunday, Oct. 11 at 3:30 PM is the $340,000 Highlands Cup Grand Prix, the biggest headline class of the weekend.
You will know when something difficult just happened because everybody around you will lose their mind.
World-class show jumping is the anchor, but not the entire assignment. Photo courtesy of Highlands Hudson Valley.
You can also just… have a day
Vendor Row, Local Eats and the Kid’s Zone run Friday–Sunday from 10 AM–4 PM. Translation: you can shop, grab food and drinks, let the kids do activities, watch a few rounds and wander back toward the arena when the crowd gets loud.
This is not six hours trapped in a bleacher pretending to understand horse stats.
Food, drinks and a place to sit are part of the day — not an afterthought. Photo courtesy of Highlands Hudson Valley.
Yes. There is an art gallery at the horse show.
The Gallery at Highlands runs Friday–Sunday from 11 AM–6 PM and is new for 2026. The $100 Gallery Experience includes premium competition views, a climate-controlled space with elevated furnishings, a complimentary Champagne Bar, contemporary painting, photography, sculpture and collectible design, plus art installations curated by internationally recognized artist Brendan Murphy.
Saturday and Sunday from 11 AM–3 PM, the Gallery adds relaxed “Gallery Moments”: drop-in artist talks, live demonstrations and conversations where guests can ask questions and hear directly from featured artists.
There is also a separate $275 Gallery VIP Experience on Sunday with premium food and beverage, enhanced lounge seating, artist panels and live exhibitions.
In other words: this is not a folding-chair add-on hiding beside the arena. It is its own art-and-hospitality experience inside the larger Highlands weekend.
The Gallery is one of the reasons Highlands makes sense for a mixed-interest group. Photo courtesy of Highlands Hudson Valley.
If you want to go full fancy, there is a version of that too
Legacy Club VIP starts at $400 and includes Legacy Club access, open seating, gourmet dining and a premium open bar. Sunday, Oct. 11 is currently sold out.
This is the upgrade for the person whose sporting-event strategy is basically: please solve lunch, drinks and comfort for me.
Legacy Club is the premium hospitality route. Photo courtesy of Highlands Hudson Valley.
Sunday is horsepower in both directions
The Bridlemont Concours runs Sunday, Oct. 11 from 10:30 AM–4 PM, bringing a curated field of automobiles, motorcycles and historic race cars onto the Highlands estate. General admission to the concours is free.
Miller Motorcars also brings an all-day exotic-car exhibition into the Grand Prix arena, followed by a 2–3:30 PM hypercar course walk. Then, at 3:30 PM, the $340,000 Highlands Cup Grand Prix starts.
So no, this is not “a few nice cars parked outside.” The automotive piece is part of the actual day.
Bridlemont puts automotive culture on the same estate as international show jumping. Photo courtesy of Highlands Hudson Valley.
Pick your Highlands day
WEDNESDAY / THURSDAY — Best for easing in. Come for the show jumping and a quieter midweek pace without trying to cram in every marquee attraction.
FRIDAY — Best for art + sport. The Gallery is open 11 AM–6 PM, and the $181,170 CSI5* qualifier starts at 1:10 PM.
SATURDAY — Best for the big team day. The Gallery is open 11 AM–6 PM, with food, shopping, Legacy Series Conversations and the $200,000 Mission Foods Racing Major League Show Jumping Team Class at 4 PM. Later that night, Highlands hosts a separate ticketed Evening of Giving.
SUNDAY — Best for maximum everything. Bridlemont, exotic cars, The Gallery from 11 AM–6 PM and the $340,000 Highlands Cup Grand Prix at 3:30 PM.
Horsepower, in more than one sense. Photo courtesy of Highlands Hudson Valley.
How to go
WHAT: Highlands Cup Week
WHEN: Oct. 7–11, 2026
WHERE: Highlands Hudson Valley, 217 Depot Hill Road, Amenia, NY 12501
FREE ENTRY: General admission is free; paid upgrades and hospitality are optional.
GALLERY: Friday–Sunday, 11 AM–6 PM; Gallery Experience $100; Sunday Gallery VIP $275.
SATURDAY HEADLINER: $200,000 Mission Foods Racing Major League Show Jumping Team Class — 4 PM.
SUNDAY: Bridlemont Concours 10:30 AM–4 PM; Highlands Cup Grand Prix 3:30 PM.
HOSPITALITY + UPGRADES: https://highlandshudsonvalley.com/hospitality-packages/
FULL HIGHLANDS CUP DETAILS: https://highlandshudsonvalley.com/the-highlands-cup/
Photo credit throughout: Courtesy of Highlands Hudson Valley.
