Amy Chesnut
Owner and Innkeeper
Amy Chesnut started coming to the Cape as a toddler – over 60 years ago! She is happy to share that there are still some places on the Cape that have not changed in all those years! Amy permanently moved to the Cape in 2016 when she purchased Brewster By The Sea Inn, located at 716 Main Street in Brewster. Prior to owning and running the Inn, Amy was an attorney and a land conservation professional, where, in 2016, she was formally recognized by the California State Legislature and the Sonoma County Board of Supervisors for her decades-long dedication to working and collaborating with partners to protect the open spaces and working lands in California. As the Acquisitions Director for Sonoma Land Trust, she managed projects on the Sonoma Coast, securing tens of millions of dollars to permanently protect the landscapes. This familiarity with natural systems, and history of securing funding, gave Amy the essential background to become a trustee on the board of the Brewster Conservation Trust between 2017 and 2022.
The people skills that Amy developed during her 30-year career were easily transferrable to hospitality, and Amy has been the face of, and operations behind, Brewster By The Sea Inn for 10 years. Brewster By The Sea Inn is open year-round, and over the many years of personally greeting each guest as they arrive at the Inn, Amy has provided thousands of people guidance about what to see and do in all four seasons – Spring, Summer, Fall and Winter. From favorite trails and beaches, to hidden spots known only to locals, Amy can tell you where to hike, walk, bike, or motor to see the best the Cape has to offer. When it comes to dining, Amy has her list of favorite restaurants throughout the 15 towns on the Cape. No matter which direction the guests may be heading, Amy can provide top recommendations on how to get there, what to do, and where to eat!
Amy is a member of the Brewster Chamber of Commerce, and received the Chamber’s (in collaboration with SCORE Cape & Islands) Small Business Excellence Award in 2026. Check out Amy’s reviews and testimonials on Google – a large portion of Amy’s guests come back year-after-year to enjoy thoughtful hospitality at its best.