Overlook Annual Fall Festival

The Overlook is a Continuing Care Community with over 400 Residents. Located in Charlton in the heart of New England, our 450-acre community is hosting its 8th Annual Fall Festival on Saturday, October 3, 2026. This public event has been a huge success, attracting thousands of attendees from Massachusetts, Connecticut, Rhode Island and beyond who enjoyed a day filled with vendor booths, live music, hayrides, games, prizes and seasonal treats. This year we are expanding with even more crafters and artists -candles, soaps, natural products, jewelry, clothing, scarves, quilts, blankets, knitted items, woodcrafts, pottery, paintings, books, tools and photography. And specialty foods, cheeses, spices, wine and beer tasting, food trucks, local restaurants, and farm stand produce.

All Ages