Private Tour

Self Guided Walking Tour of Oak Bluffs Marthas Vineyard

Overview

Available languages

English

Mobile ticket

Unearth the charm of Oak Bluffs on this self-guided walking tour, where the rich history and vibrant culture of this New England seaside town come alive.

Wander among whimsical gingerbread cottages, enjoy stunning harbor views, and learn how this area evolved from a Methodist camp meeting site to a celebrated resort.

This tour highlights the unique blend of architecture, community spirit, and African American heritage that defines Oak Bluffs, making it a delightful exploration of summer memories and local stories.

— Discover the distinctive Victorian architecture and intricate cottages

— Explore the historical significance of Oak Bluffs as a cultural hub

— Enjoy scenic ocean views and shaded park paths during your stroll

— Perfect for history buffs and those seeking a unique coastal experience

Additional Info

Infants and small children can ride in a pram or stroller

Suitable for all physical fitness levels

Works entirely offline once downloaded—no cell service required

GPS-triggered audio plays automatically based on your location

Flexible - Buy once, use any day/time—access never expires

Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

What‘s Included

Flexible Usage (unlimited access)

Audio Guide & Route Map (in-app)

App and Tour Download

Smartphone (bring your own)

What To Expect

Cottage Museum

Step inside this tiny museum to see what life was like in a 19th-century “gingerbread cottage,” complete with original furnishings and period charm. The adjoining shop offers locally made crafts and souvenirs that capture the whimsy of Oak Bluffs.

5 minutes • Admission Not Applicable

Circuit Avenue

The lively heart of Oak Bluffs, Circuit Avenue, hums with summer energy, from old-fashioned ice cream parlors to boutique shops and cafés. It’s the perfect place to stroll, people-watch, and soak up the festive Vineyard atmosphere.

5 minutes • Admission Not Applicable

Options