For 40 years, Oak Bluffs has celebrated Tivoli Day, a home-grown end of summer celebration. The event began as a bicycle race, and has evolved into a street fair featuring music, dining, vendors, face painting, and more. The 40th anniversary celebration was dedicated to the late Ed Coogan and Michael Wild, who were credited with founding Tivoli Day.

The name comes from the long gone but not forgotten Tivoli Dance Hall, which gained fame in the roaring 20s. This year's event did not feature the Charleston or the jitterbug, but spirits were high nonetheless as Circuit avenue was filled with artisans and shop-owners selling their wares, children dancing with freshly-painted faces, and revelers carrying shopping bags and stopping to listen to music, enjoying the pace of September on the Vineyard.