Main Street Penn Yan has a way of inviting you in with open arms and open doors. Locally owned storefronts and friendly hellos make it a place where wandering feels natural and unhurried. Among the many small businesses that give Main Street its character are women-owned shops built around creativity, family and quality. 

From thoughtfully curated and inclusive clothing to handcrafted goods made from reclaimed materials, Simplicity on Main and Staving Artist Woodwork are amongst the many shops along Main Street that offer visitors a meaningful way to experience shopping in the Finger Lakes Countrysides—one that feels personal, welcoming, and rooted in real life. 

When Simplicity opened in 2018 (not on Main Street yet!), it was born from a desire to create something both practical and personal. The owner, Lauren McQuaid, loved her career as a hairstylist, but she also dreamed of building a business that allowed her to spend more time with her growing family. That vision led her to open a women’s clothing boutique designed to make shopping feel easier, more comfortable, and more inclusive. 

Simplicity on Main offers a wide range of styles and sizes meant to help shoppers feel confident without feeling overwhelmed or priced out. For many customers, especially those who have struggled with online shopping, being able to try things on in person has been a gamechanger. Since opening a downtown location in 2025, visitors often share how much they love being able to browse, try things on and leave feeling confident in their choices. 

 

Inside the shop, the atmosphere is relaxed and thoughtfully organized. First-time visitors are often surprised by the variety available, and regulars appreciate how approachable the experience feels. Denim has become a particular point of pride, with many shoppers sharing how rare it is to find jeans that are comfortable, reliable, and truly flattering. 

Being in downtown Penn Yan was a long-held goal, and when the opportunity finally presented itself, the timing felt right. With Lauren’s children now school-aged, opening a brick-and-mortar shop allowed her to grow the business while staying aligned with family priorities. That balance is intentional. The owner has been open about closing early or adjusting hours to be present for her children, even when it means navigating slower seasons. For her, success has never meant choosing between work and family —it’s meant finding a way for her to honor both. 

Beyond clothing, Simplicity on Main aims to be a positive, welcoming presence on Main Street. Every shopper who walks through the door is meant to feel seen, supported, and comfortable. 

 

Staving Artist Woodwork began as a blend of long-held creativity and real-life necessity for owner Rachel Orlyk and her husband, Dan Mitchell. After the birth of their son in 2016, the realities of balancing work, childcare, and family life led to a turning point. While Dan had been honing his woodworking craft for years, where he uniquely uses reclaimed winemaking materials to create one-of-a-kind pieces (a perfect fit running a business amongst a booming wine industry)—the idea of opening a shop slowly became more tangible. 

When a storefront became available on Main Street in Penn Yan in 2017, the couple decided to take a leap. Opening the shop allowed them to shape their work thoughtfully around family life and building something sustainable over time. 

Today, Staving Artist Woodwork is a space centered around handmade goods, reclaimed wood pieces and original works created by Dan, as well as items from other small makers and businesses. Visitors can find custom and hand-crafted wine barrel stave pieces, trays, wall art and more. The shop has a presence that feels lived-in and intentional. Many visitors comment on the smell when they first walk in – a unique combination of wine-soaked wood, natural oils, candles, and soaps that reflect the materials and care behind each item. 

 

 

People often enter the shop without a plan. Some are searching for a meaningful gift; others are simply wandering Main Street. Whether they leave with a custom piece, multiple items, or just a moment of pause, the goal is for the experience to feel genuine. 

Being part of downtown Penn Yan means being woven into everyday life. The rhythm of the street changes with the seasons, and familiar faces return year after year. For Rachel, running a business here feels deeply personal. Yates County’s sense of community and appreciation for small businesses make it a place where relationships grow naturally. 

One of the most meaningful aspects of the work comes from creating custom pieces tied to important milestones. When customers pick up a finished piece and realize it’s exactly right, those moments carry weight beyond the object itself. Being trusted with that level of intention and care is something the business values deeply. 

Simplicity on Main and Staving Artist Woodwork are just two examples of how women-owned businesses help shape the heart of downtown Penn Yan. Each shop tells a different story, but both are rooted in creativity, community and a commitment to doing things with care. 

Check out these other women-owned shops: 

• The Nest Egg
• The Flower Cart & Gift Shoppe
• Art Studio 126 Main
• Plants on Main
• Keuka Outlet
• Judd’s Sudds.  

When you spend time shopping in the Finger Lakes Countrysides, you’re not just picking up something to take home—you’re supporting families, values, and small businesses that make places like Penn Yan feel special. Take your time, wander Main Street, and discover the stories behind the storefronts.