Setting pretty: The 18 most beautiful places in Charlottesville

Saunders-Monticello Trail. Photo: Jack Looney Saunders-Monticello Trail. Photo: Jack Looney

A few years ago, after a friend had recounted a particularly less-than-desirable day, he followed up the story with a bright spot: “But my favorite tree in town is finally blooming,” he said. I never let that “regal, purple, perfect” tree on 29S (right at the 250 overpass) go unnoticed after that. If this tree could get him looking through rose-colored glasses, it was something special. But he’s not the only one to recognize the somethings special in this town. For this year’s Design Annual, we asked eight of the area’s keenest eyes in the fields of residential, commercial, landscape, and interior design to pony up their definitive lists of the most aesthetically notable spots in Charlottesville and its surrounding counties, public and private, old and new—from Jeffersonian estates to the most beautiful magnolia on Grounds. Don’t see your favorite spot on the list? Comment on this story on and start the discussion.—Caite White, with reporting by Stephanie DeVaux

Our panel

Cathy Clary consults and teaches about the residential landscape in and around Albemarle County.

Jeff Dreyfus is the co-founder of Bushman Dreyfus Architects, which focuses its practice on institutional work for public and private clients. BDA designed such places as the City Center for Contemporary Arts and Pippin Hill Farm & Vineyards.

Lynn Easton is the founder of Easton Events, and co-owner of Pippin Hill Farm & Vineyards, Zero George (in Charleston, South Carolina), and the upcoming Red Pump restaurant. Her work has been featured in national magazines including The Knot, Southern Living Weddings, and Martha Stewart Weddings.

Allison Ewing co-owns Hays + Ewing Design Studio with her husband, Christopher Hays. A graduate of the Yale Graduate School of Architecture, Ewing has more than 33 years of architecture experience.

Peter Hatch is a professional gardener and historian with 38 years experience in the restoration, care, and interpretation of historic landscapes. He has written four books on the gardens of Monticello, where he served as director of gardens and grounds for 35 years.

Andrea Hubbell is a Charlottesville-based photographer with a background in architectural design. Her work has been featured in C-VILLE, The Scout Guide, Edible Blue Ridge, and on, a food-focused project she co-founded with fellow photographer, Sarah Cramer-Shields.

Phyllis Joseph is the owner of Joseph Joseph & Joseph, a three-generation fine antiques and architecturals retailer.

Dan Zimmerman is the co-founder of Alloy Workshop, a Charlottesville-based architecture firm that specializes in everything from design to construction. Started in 2006, it counts Commonwealth Restaurant & Skybar and Rise Pizzaworks (now called Slice) among its notable projects.