OCTOBER 7 to 11, 2026 | Amenia, New York

Horsepower, Culture, and Competition

Anchored by Major League Show Jumping team competition, The Highlands Cup blends world-class sport with exceptional hospitality, art, automotive culture, and unforgettable moments throughout the week.

Prize List
Hospitality

Highlands Cup Weekend

The Pursuit of Excellence

From Major League Show Jumping and championship competition to curated dining, live entertainment, shopping, and unforgettable social experiences, every day offers something worth discovering.

September 30, 2026

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7:30 AM

FEI CSI3* HORSE INSPECTION

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September 30, 2026

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7:30 AM – END OF COMPETITION

LEGACY CLUB

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September 30, 2026

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8:00 AM

131 – 1.30M JUMPER

Table II.2.1. One round against the clock.
Order of Go & Results
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September 30, 2026

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10:00 AM – 4:00 PM

VENDOR ROW & LOCAL EATS

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September 30, 2026

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10:00 AM – 4:00 PM

KID’S ZONE

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September 30, 2026

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11:00 AM

141 – 1.40M JUMPER

presented by INEOS
Table II.2b. Immediate jump-off.
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September 30, 2026

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2:00 PM

301 – $31,100 1.45M TWO-PHASE CSI3*

FEI 222.1.4.3. Two phase, both against the clock.
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September 30, 2026

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4:30 PM

199 – 1.15M JUMPER WARM-UP

Table II.2c. Two-phase, power and speed.
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September 30, 2026

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5:30 PM-7:30 PM

GROOM WELCOME ASADO

presented by Paul Tracy
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October 1, 2026

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8:00 AM

132 – 1.30M JUMPER

presented by Maarten Huygens Horse Sales.
Table II.2.1. One round against the clock.
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October 1, 2026

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10:45 AM

142 – 1.40M JUMPER

presented by INEOS
Table II.2.1. One round against the clock.
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October 1, 2026

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1:45 PM

302 – $31,100 1.45M SPEED CSI3*

FEI 222.1.4.3. Two phases, both against the clock. Grand Prix Qualifier.
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October 1, 2026

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4:30 PM

121 – 1.20M JUNIOR/AMATEUR JUMPER

Table II.2.1. One round against the clock.
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October 2, 2026

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8:00 AM

111 – 1.10M JUNIOR/AMATEUR JUMPER

presented by Champion Shavings. Table II.2b. Immediate jump-off.
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October 2, 2026

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10:10 AM

122 – 1.20M JUNIOR/AMATEUR JUMPER

presented by Bosch Sport Horses
Table II.2b. Immediate jump-off.
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October 2, 2026

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10:00 AM – END OF COMPETITION

GALLERY

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October 2, 2026

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1:10 PM

303 – $62,500 1.50M JUMPER CLASSIC CSI3*

presented by Stoneleaf
FEI 220.2.1.2.1.50m. Table A, one round against the clock with one jump-off against the clock
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October 2, 2026

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4:40 PM

101 – 1.0M JUNIOR/AMATEUR JUMPER

Table II.2.1. One round against the clock.
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October 2, 2026

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6:00 PM-8:30 PM

RIDER WELCOME PARTY

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October 2, 2026

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EQUUS EFFECT FUNDRAISER

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October 3, 2026

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8:00 AM

102 – 1.0M JUNIOR/AMATEUR JUMPER

Table II.2.1. One round against the clock.
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October 3, 2026

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9:30 AM

112 – 1.10M JUNIOR/AMATEUR JUMPER

presented by Alliant Private Client
Table II.2.1. One round against the clock.
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October 3, 2026

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11:30 AM

133 – 1.30M JUMPER CLASSIC

presented by Frank & Eileen
Table II.2a. Return for jump-off.
📍
October 3, 2026

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3:15 PM

143 – 1.40M JUMPER CLASSIC

presented by INEOS
Table II.2a. Return for jump-off.
📍
October 4, 2026

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8:00 AM

103 – 1.0M JUNIOR/AMATEUR CLASSIC

presented by Daily Harvest
Table II.2b. Immediate jump-off.
📍
October 4, 2026

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9:30 AM

113 – 1.10M JUNIOR/AMATEUR CLASSIC

presented by Skyline Windows
Table II.2b. Immediate jump-off.
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October 4, 2026

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11:30 AM

123 – 1.20M JUNIOR/AMATEUR CLASSIC

presented by YETI
Table II.2a. Return for jump-off.
📍
October 4, 2026

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3:15 PM

304 – $116,500 1.50M GRAND PRIX CSI3*

presented by Discovery Land Company
FEI 220.2.1.2GP. 1.50m. Table A, one round against the clock with one jump-off against the clock. Qualification for the Grand Prix will be based on the best results from competition 302 and 303. One horse per rider.
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October 4, 2026

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5:15 PM

Grand Prix Awards & Podium Ceremony

Leading Lady Rider presented by Cara Cara
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October 1, 2026

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7:30 AM – END OF COMPETITION

LEGACY CLUB

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October 1, 2026

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10:00 AM – 4:00 PM

VENDOR ROW & LOCAL EATS

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October 1, 2026

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10:00 AM – 4:00 PM

KID’S ZONE

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October 2, 2026

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7:30 AM – END OF COMPETITION

LEGACY CLUB

📍
October 2, 2026

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10:00 AM – 4:00 PM

VENDOR ROW & LOCAL EATS

📍
October 2, 2026

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10:00 AM – 4:00 PM

KID’S ZONE

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October 3, 2026

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7:30 AM – END OF COMPETITION

LEGACY CLUB

📍
October 3, 2026

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10:00 AM – 4:00 PM

VENDOR ROW & LOCAL EATS

📍
October 3, 2026

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10:00 AM – 4:00 PM

KID’S ZONE

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October 4, 2026

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7:30 AM – END OF COMPETITION

LEGACY CLUB

📍
October 4, 2026

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10:00 AM – 4:00 PM

VENDOR ROW & LOCAL EATS

📍
October 4, 2026

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10:00 AM – 4:00 PM

KID’S ZONE

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October 7, 2026

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7:30 AM

FEI CSI2*/5* HORSE INSPECTION CSI2* horses first

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October 7, 2026

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7:30 AM – END OF COMPETITION

LEGACY CLUB

📍
October 7, 2026

|

8:00 AM

134 – 1.30M JUMPER

Table II.2b. Immediate jump-off.
📍
October 7, 2026

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10:00 AM – 4:00 PM

VENDOR ROW & LOCAL EATS

📍
October 7, 2026

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10:00 AM – 4:00 PM

KID’S ZONE

📍
October 7, 2026

|

10:30 AM

144 – 1.40M SPEED JUMPER

Table II.2.1. One round against the clock.
📍
October 7, 2026

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1:00 PM

201 – $6,820 1.40M WELCOME TWO-PHASE CSI2*

presented by Equiratings
FEI 222.1.4.3. Two phase, both against the clock.
📍
October 8, 2026

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7:30 AM – END OF COMPETITION

LEGACY CLUB

📍
October 8, 2026

|

8:00 AM

135 – 1.30M JUMPER SPEED

Table II.2.1. One round against the clock.
📍
October 8, 2026

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10:00 AM – 4:00 PM

VENDOR ROW & LOCAL EATS

📍
October 8, 2026

|

10:00 AM – 4:00 PM

KID’S ZONE

📍
October 8, 2026

|

10:15 AM

145 – 1.40M JUMPER CLASSIC

Table II.2a. Return for jump-off.
📍
October 8, 2026

|

1:30 PM

202 – $31,020 1.45M SPEED CSI2*

FEI 220.2.1.1. One round against the clock.
📍
October 8, 2026

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4:30 PM

501 – 1.40M WARM-UP TWO-PHASE CSI5*

FEI 222.1.4.3. Two phase, both against the clock.
📍
October 9, 2026

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7:30 AM – END OF COMPETITION

LEGACY CLUB

📍
October 9, 2026

|

8:00 AM

124 – 1.20M JUNIOR/AMATEUR JUMPER

presented by Klocke Estate
Table II.2.1. One round against the clock.
📍
October 9, 2026

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10:00 AM – 4:00 PM

VENDOR ROW & LOCAL EATS

📍
October 9, 2026

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10:00 AM – 4:00 PM

KID’S ZONE

📍
October 9, 2026

|

10:00 AM

203 – $40,000 1.45M GRAND PRIX CSI2*

presented by Go Rentals
FEI 220.2.1.2GP. 1.45m. Table A, one round against the clock with one jump-off against the clock. Qualification for the Grand Prix will be based on the best results from competition 202. One horse per rider.
📍
October 9, 2026

|

1:10 PM

502 – $181,170 1.50M GRAND PRIX QUALIFIER CSI5*

presented by Airshare
FEI 220.2.1.2. 1.50m. Table A, one round against the clock with one jump-off against the clock.
📍
October 10, 2026

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7:30 AM – END OF COMPETITION

LEGACY CLUB

📍
October 10, 2026

|

8:00 AM

104 – 1.0M JUNIOR/AMATEUR JUMPER

presented by Milea Estate Vineyards
Table II.2.1. One round against the clock.
📍
October 10, 2026

|

9:30 AM

114 – 1.10M JUNIOR/AMATEUR JUMPER

presented Frank & Eileen
Table II.2.1. One round against the clock.
📍
October 10, 2026

|

10:00 AM – 4:00 PM

VENDOR ROW & LOCAL EATS

📍
October 10, 2026

|

10:00 AM – 4:00 PM

KID’S ZONE

📍
October 10, 2026

|

11:30 AM

125 – 1.20M JUNIOR/AMATEUR CLASSIC

presented by B&D Builders
Table II.2b. Immediate jump-off.
📍
October 10, 2026

|

2:30 PM

503A – $31,100 MAJOR LEAGUE SHOW JUMPING INDIVIDUAL CSI5*

MLSJ RULES. Same course as first Team Round.
📍
October 10, 2026

|

4:00 PM

503B – $200,00 MISSION FOOD RACING MAJOR LEAGUE SHOW JUMPING TEAM CLASS CSI5*

presented by ClipMyHorse
MLSJ RULES.
October 10, 2026

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MAJOR LEAGUE SHOW JUMPING TEAM AWARDS & PODIUM CEREMONY

Classes 104,114,125 National Awards
October 10, 2026

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“An Evening with Highlands” Charity Event

Featuring Angels of Light, Road to the Top, & The Person First
October 10, 2026

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1:30 PM

COURSEWALK FEATURING MISSIOMN FOODS RACECAR DISPLAY

October 11, 2026

|

8:00 AM

104 – 1.0M JUNIOR/AMATEUR JUMPER CLASSIC

presented by Alliant Private Client
Table II.2b. Immediate jump-off.
📍
October 11, 2026

|

9:30 AM

115 – 1.10M JUNIOR/AMATEUR JUMPER CLASSIC

presented by GGT Footing
Table II.2b. Immediate jump-off.
📍
October 11, 2026

|

$31,100 1.45M BRIDLEMONT WINNING ROUND CSI5*

presented by Cabana Coast
October 11, 2026

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2:00 PM

COURSEWALK FEATURING MILLER MOTORS HYPECAR DISPLAY

October 11, 2026

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$340,000 1.60M HIGHLANDS CUP GRAND PRIX CSI5*

presented by Miller Motors
October 7, 2026

|

5:30 PM-7:30 PM

GROOM WELCOME ASADO

presented by Higher Ground Farm
📍
October 9, 2026

|

6:00 PM-8:30 PM

RIDER WELCOME PARTY

📍
October 11, 2026

|

7:30 AM – END OF COMPETITION

LEGACY CLUB

Order of Go & Results
📍

HOSPITALITY EXPERIENCES

Premium hospitality options offer unparalleled views, signature service, and exclusive access throughout the event. Designed for connection and celebration, Highlands hospitality provides the perfect backdrop for client entertainment, social gatherings, and special occasions.

HOSPITALITY PACKAGES
Aerial view of arenas, fields, and barns

DISCOVER THE HUDSON VALLEY

The Highlands Cup is the perfect reason to explore one of New York’s most celebrated destinations. Enjoy luxury accommodations, farm-to-table dining, wineries, outdoor recreation, and charming local communities throughout your stay.

VIEW, EAT, STAY
Shelf with mugs, glasses, and bottles set between racks of clothing.

VENDOR OPPORTUNITIES

Businesses interested in reaching a highly engaged audience can apply to participate in the event’s curated vendor experience.

VENDOR INFORMATION

Media Inquiries

Members of the media seeking interviews, press materials, photography, or additional information are encouraged to contact the Highlands team.
Contact Media
PRIVATE PHOTOGRAPHER APPLICATION

Extraordinary Relationships

Event
Partners

Together with our partners, we continue to create extraordinary relationships that celebrate sport, community, and hospitality.

Our Partners

The Good Dog
Yeti
Mission Foods
Barnwalkers + IDA
Stoneleaf logo
Milea Estate Winery
Discovery Land Company
Miller Motor Cars
Brendan Murphy
Skyline Windows
The Person First
Grace View Farm
Morrissey Management Group
Champion
The Equus Effect
Paragon Roofing
Baobab Collection
Stone Crafting
Wood Crafting
Horse Pilot
EquiScore
Franklin Hardware
Cara Cara
Go Rentals
Klocke Estate
Ineos Grenadier 2
Horse Flight
CWD
Monticello
Equiratings
Liquid Death
Roche Bobois
Paul Tracy
McLain Ward
Major League Show Jumping
Bosch Sporthorse
Tasu
Airshare
PCAR Market
My Mancini
B & D Builders
Jessica Gersten Design
Maria Mendesohn logo
STX
Andrew Franz
Happy Hen
La Colombe
Fairfield – North Star
North Ridge Painting
Partnership Inquiry

Email:  info@highlandshorseshow.com
for Partnership Inquiry