Professional cleaners, prepare to embark on a captivating journey through time on the enchanting Martha's Vineyard. While the island today exudes tranquility and charm, its rich history as a haven for mariners, whalers, and seafaring souls of yore offers a plethora of fascinating sights and experiences. From centuries-old settlements to architectural gems adorned with captivating tales, every brick and arched roof tells a unique story that enhances the picturesque beauty of this destination.

While there are numerous walking tours available in Martha's Vineyard, we understand that time constraints or a desire for a more leisurely exploration may lead you to venture at your own pace. Fear not, for we have curated a list of our cherished historical gems on both islands. These extraordinary places beckon you to immerse yourself in their narratives and uncover the secrets that have shaped their identity. So, without further ado, let us unveil the wonders that await you on this historical odyssey!

Gingerbread Cottages of Oak Bluffs

A colony of perfectly preserved Carpenter Gothic styled cottages, popularly known as gingerbread cottages and dating back to the mid-1800s, is what dots the center of Oaks Bluffs. This collection of fairytale houses are still owned and inhabited by generations of families descended from the original Martha’s Vineyard Camp Meeting Association, and their humble beginnings are still reflected in their tightly clustered together interiors and lack of private yards both front and back. Now they’re one of the most photographed houses in America, and how could they not be? They’re adorable!

Old Whaling Church

An impressive example of Greek Revival architecture in New England, the Old Whaling Church was originally built for Edgartown’s Methodist captains, but now stands as a testament to the town’s seafaring roots and the wealth that the whaling business brought with it. Mimicking an ancient temple with its six enormous Doric temples and crowned with a Gothic Revival clock tower, the Church is a living example of the style that dominated American architecture for decades in the 1800s. This beautiful building is one of the most notorious stops of the many walking tours around Edgartown, so you shouldn’t miss it.

Edgartown Lighthouse

More than just pretty vestiges of a bygone era, the lighthouses of Martha’s Vineyard (East Chop, Edgartown and Gay Head) are still-functioning beacons that shine-out to the sea every night. Thankfully, they’re also open to the public since they’re stewarded by the Martha’s Vineyard Museum, and offer their amazing views on the Edgartown Harbor, Chappaquiddick, and the cliffs of Aquinnah. The Edgartown lighthouse underwent renovations to allow visitors inside and up on the lantern room, and tours are available year-round.

Dr. Daniel Fisher House

Once owned by Dr. Daniel Fisher, who was one of the wealthiest men in America at the height of the whaling era, this Federal style residence has transformed over the years to include a beautiful garden on the west side, with an onion-domed roof gazebo ornamented with a gilded pineapple which you really can’t miss during your visit, and the inside of the house proper is so beautifully kept that you’ll want your house to look the same! Further, on the northeast corner, lies a sunken water garden, which compliments nicely with the beautiful surrounding areas.