Look who goes there! Is that OLIVE WESTCHESTER? I’ve seen them often around SADDLE GROVE, which may be because they are a OWNER AND OPERATOR OF WESTCHESTER FAMILY FARM. They’ve been in town for THIRTY-TWO YEARS and I’ve known them to be HARDWORKING but also HYPER-INDEPENDENT. For some reason, SWIMMING by MAPLE GLIDER reminds me of them, as well as WEATHER JOURNALS DATING BACK DECADES, HOMEMADE SOURDOUGH EXPERIMENTS, & FADED BASEBALL CAPS.
OVERVIEW
Full Name: Olive Celeste Westchester
Birthday: March 26, 1990 (36 years old)
Birthplace/Hometown: Bear Creek, Colorado
Current Residence: Saddle Grove - 3.5 acre lot (3Bd, 2Ba) since August 2020
Occupation: Owner and Operator of Westchester Family Farm
Education: B.S. Agribusiness and MS of Agribusiness & Food Innovation Management at Colorado State University (Fort Collins)
Family: Peter Westchester (Father) , Annabelle Westchester (Mother) & Briar Rose Westcher (Sister, @briarrosew), Remy Weschester (1-year old Nephew), Banjo (6-year old Australian Shepherd) and Fig (8-year old Shorthair)
Relationship Status: Single (Heterosexual)
Personality: Dependable. Hardworking. Self-sufficient. Curious. Loyal. Extremely blunt. Competitive. Restless. Stubborn. Bottles emotions. Can unintentionally intimidate people. Gets bored quickly.
OLIVE'S STORY
For months, everyone assumed the beloved Peter and Annabelle Westchester of Bear Creek, Colorado's firstborn, would be a son. When she arrived, her father laughed and then cried before dropping one letter off the original name. Olive. She was a mirroring image of her father. The same dark hair, same stubborn expression, and sharp eyes that looked out into the world with ambition. He had a feeling she'd be a powerhouse.
Her father was born and raised on the Westchester Family farm. As one of the founding families, the Westchester roots are embedded deep in the town. They built a dynasty dedicated to building a legacy of fresh meat, produce, and the finest animals not only in the state of Colorado, but across the country. Her mother, a vivacious Australian, was charmed by this Coloradan at an agricultural conference in the 80s, and the rest is history.
Olive grew up alongside her sweet baby sister between cattle pastures and vineyard rows with scraped knees, muddy boots, a sharp tongue, and a sly grin. She quickly learned that what the Westchesters established, as well as what her mother maintained, was rooted in stewardship. Every season demanded patience, love, adaptability, and respect for whatever the land and nature provided any given year.
As she got older, she began helping repair fences at age seven, driving farming equipment by thirteen, and helping with branding season and the county fairs in between her sports and studies once she hit high school. There was no better place to be in her opinion than the farm. Olive was dedicated in every way to keep the family legacy alive and expand it beyond the reaches of Bear Creek one day.
Finishing off high school with a 4.0 and recruitment for D1 soccer, Olive headed off to college in hopes to do better by the family name. College expanded her horizons in ways she never would have thought. She found herself entranced by farming technology, conservation strategies, and restorative agriculture. There were opportunities for her to take her knowledge elsewhere, highly encouraged by her professors, but there was no better place to be than Bear Creek.
A slew of ideas later, from diversifying crops, providing tourism experiences, educational programming, and expanding their reach beyond Denver, Olive has poured herself into the farm. Since the age of twenty-two, she’s been working hand in hand with her father and team, implementing changes and earning her keep and right to opinions. A year ago, she was handed ownership when her father retired, and since then has been working tirelessly to grow the Westchester name beyond Colorado, keeping their integrity intact in the process.
Outside of work, her personal life seldom has anything noteworthy to mention. She's dated a handful of boys to know what she doesn't want, loves meeting newbies and tourists in town, and has her solid squad of friends that is an extension of her family. She lives a quiet life despite her friend teasing that it's because she's too prickly. Nonetheless, every sunrise is another opportunity to be better than the day before, and damn it, she's gonna try.
*Headcanons & Connections












