Brandon is steeped in history, including its recognition as the birthplace of Stephen Douglas. The town offers a self-guided walking tour throughout the village. Highlights include stately architecture in more than 200 buildings, historical landmarks such as the Stephen Douglas birthplace, boutique shops selling a variety of Vermont products and a roaring waterfall right in the center of town. There are several restaurants located within the tour area, including the famed Cafe Provence. Brandon also boasts several covered bridges on the outskirts of town.
Former Vermont Governor, Jim Douglas, dubbed Brandon as the "art and soul" of Vermont. Downtown Brandon is awash with galleries and antique shops. The town is home to renowned artist Warren Kimble, and his work is on display at his downtown gallery. The Brandon Artists Guild is open to the public for viewing the works of more than 50 local artists. For adventurous seniors, some of the studios offer art classes as well.
Though Brandon is small in size, its shopping offerings are plentiful. Locally-owned boutique shops offer many one-of-a-kind items. Briggs Carriage Bookstore offers comfortable seating where shoppers take time out to rest or relax. The store also offers nightly chess games and a weekly knitting circle. The famed New England Maple Museum displays the history of maple sugaring, along with a gift shop carrying a wide variety of maple products for purchase. Seniors also enjoy Wood's Farmers Market, where they purchase locally-grown produce and get cozy with alpacas and goats.
Brandon has a vibrant community that offers ongoing events that seniors enjoy. The Brandon Free Public Library hosts literary events and a Friday movie. The Brandon town band, with members of all ages, performs on Mondays in the park, weather permitting. The Inside Scoop, a local ice cream parlor, offers Spanish conversation groups on Saturday mornings for those wishing to learn the language.