Faces Behind the Storefront: Kelsey Settle of Green Roost

The Vision Behind Green Roost

In the heart of downtown Culpeper, Green Roost has become a destination for shoppers looking for thoughtful gifts, sustainable products, and brands that make a difference. Behind the shop is Kelsey Settle, a local entrepreneur whose journey reflects the power of mentorship, resilience, and community.

A Business Rooted in Family

Green Roost’s story began as a family endeavor. The shop was originally started by Kelsey’s aunt, Sharon Clark, owner of Pepperberries. Kelsey managed the store during its early years under her aunt’s guidance before officially becoming the owner in 2011. While she once imagined a life in the city, Culpeper quickly changed those plans. “I often say that I didn’t choose Culpeper – Culpeper chose me.” That unexpected connection to small-town life would ultimately shape both her career and the direction of the business.

Retail with a Purpose

Early in her journey as a business owner, Kelsey realized she wanted Green Roost to be more than just a retail shop. She began focusing on brands that make a positive impact. One of the first partnerships that influenced her perspective was with TOMS shoes. Seeing how every purchase could contribute to a greater cause changed the way she thought about retail. That experience inspired Kelsey to curate a store centered around products that give back, brands that combine style, sustainability, and social impact. Today, Green Roost continues to reflect that mission.

Overcoming Early Challenges

Like many entrepreneurs, Kelsey’s path wasn’t without obstacles. In the early days, she faced an unexpected legal hurdle when a trademarked company required her to change the store’s name from Green Nest to Green Roost. Not long after, the 2011 Virginia earthquake caused significant damage to the shop. These early setbacks quickly taught her an essential lesson in entrepreneurship: adaptability matters. Rather than slowing down, those challenges strengthened her resolve and shaped her approach to business.

Inspired by Women Entrepreneurs

Throughout her career, Kelsey has been inspired by the strong women around her who have shaped her leadership and outlook on business. “I firmly believe that women can move mountains,” Kelsey says. From fellow entrepreneurs to mentors and family members, she has seen firsthand how women can create meaningful change when they support one another and invest in their communities. Her Aunt Sharon’s entrepreneurial journey was one of her earliest inspirations, while her mother’s remarkable work ethic continues to influence the values she brings to her business every day.

A Commitment to Community

For Kelsey, being part of Culpeper’s small business community means more than simply operating a store. Over the years, she has served on the boards of several local organizations, including Culpeper Renaissance Inc., the Culpeper Wellness Foundation, and the Free Clinic of Culpeper. She has also been actively involved with Career Partners through the E Squared program, helping mentor the next generation of entrepreneurs. This commitment reflects her belief that businesses thrive when they stay connected to the communities that support them.

Celebrating Longevity and Growth

Green Roost recently celebrated 17 years in business, a milestone Kelsey is incredibly proud of. For her, longevity represents more than time it reflects a willingness to grow as a business owner and step outside her comfort zone. In recent years, she joined a global peer mastermind group, gaining support and insight from fellow women entrepreneurs who continue to challenge and inspire her.

Looking Ahead

Kelsey is also expanding beyond the storefront. She recently launched AWAREties, a product-based brand centered on hair accessories that combine style with social impact. The line debuted at Green Roost and is already being carried in boutiques across the country, an exciting step for a brand that began in a small downtown shop in Culpeper, VA.

Advice for Women Entrepreneurs

For women considering starting a business in a small town, Kelsey emphasizes the importance of relationships. Lean on the women around you. Ask questions. Show up at meetings. Be part of the community. Small towns thrive on connection and when business owners invest in those relationships, support often follows.

Life Beyond the Store

When she’s not at Green Roost, Kelsey enjoys spending time at home with her husband, Chris, and their two sons, Harrison and Grant. Though she describes herself as both a homebody and a traveler, you’ll usually find her at the shop, with her family, or planning her next adventure somewhere new.

Through thoughtful leadership, community involvement, and a passion for purpose-driven retail, Kelsey Settle continues to shape Green Roost into more than just a shop it’s a reflection of the values that make Culpeper’s small business community so special.