Scott Scheleur
Google
Great history to learn about and a beautiful residential area to walk through, iconic for Oak Bluffs. If you can go on a guided walking tour with the association, we highly recommend it. The tours are led by residents and the history and personal experiences you hear on the tour are wonderful and a bargain at $15 per person for 1.5 hours walking tour (no pre-registration, just show up 15 minutes before tour time at the historic open air Tabernacle). The tour ends at the Cottage Museum ($3 entrance fee is included in tour fee), which allows you to go inside a cottage that is filled with antiques and pictures…and also lovely docents/residents who have a set history speech, but will also answer questions. Even if you can’t do the guided walking tour, go wander around on your own through the maze of streets. The gingerbread, the paint colors, the flowers, the theme houses, and the architecture are all wonderful and a new surprise around every turn. Just remember, people live in these houses, so be respectful.