December 7, 2023 in Massachusetts

Uncovering the Rich History of Oak Bluffs, Massachusetts

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Early History

The land that is now Oak Bluffs was originally inhabited by Native Americans, including the Wampanoag tribe. Archaeological evidence shows the Wampanoag had settlements on Martha’s Vineyard for over 10,000 years before European contact. They lived an agricultural and maritime lifestyle, fishing the surrounding waters and growing crops like corn, beans, and squash.

The Wampanoag called the area “Ohkemmo” which meant “bent grass” referring to the saltwater marshes along the coastline. They had seasonal camps throughout the island and a main village site near the eastern shore. The Wampanoag thrived on Martha’s Vineyard until the 1600s when European colonization and disease severely impacted their population. Though much reduced, their descendants still have a presence on the island today.

Colonial Settlement

The town of Oak Bluffs began as a part of Edgartown, settled by English colonists in 1642. Edgartown was officially incorporated in 1671 and was one of the three original Cape Cod towns formed by Puritan settlers, along with Barnstable and Sandwich.

The area now known as Oak Bluffs was called Herring Creek and was used by the Wampanoag tribe for fishing before English settlement. The first English settlers were led by Thomas Mayhew Jr., who purchased the land from the Earl of Sterling. Early settlers relied on fishing, whaling and farming to sustain the community.

Throughout the 17th and 18th centuries, Herring Creek remained a small farming village within Edgartown. The inland areas were mainly dense woodlands. Development was slow during this period, but the community grew through the addition of homes, mills, schools and churches. By the late 18th century, Herring Creek had about 500 residents who lived off the sea and the land.

19th Century Growth

The 19th century saw rapid population growth and economic development in Oak Bluffs. The construction of new wharves and the town’s harbor attracted shipbuilding and fishing industries.

In the early 1800s, local shipyards produced over 30 fishing and whaling vessels along the harbor. This brought an influx of sailors and ship builders to Oak Bluffs. The town’s fishing fleet grew steadily, harvesting mackerel, cod, and lobsters from Vineyard Sound.

Oak Bluff’s strategic location made it an important hub for trade. Local merchants did brisk business supplying ships and feeding the growing population. As the economy expanded, banks, schools, churches and civic organizations were established.

By mid-century, steamboats provided easy transportation to the mainland. Improved roads and railroads connected Oak Bluffs to other parts of the island. The cranberry industry thrived in the area’s acidic bogs. Oak Bluffs had grown into a prosperous maritime village by the late 1800s.

Tourism Begins

In the mid-19th century, Oak Bluffs started to become a popular summer resort destination. The first hotels were built to accommodate the influx of tourists arriving by steamship from the mainland. The Ocean View House opened in 1847 as one of the first hotels in Oak Bluffs. Located along the shoreline, it provided beautiful views of Nantucket Sound for the well-to-do clientele.

More hotels soon followed to meet the demands of tourism. The elegant Wesley House opened in 1866, advertising itself as a “first class summer resort.” The nearby Martha’s Vineyard Camp Meeting Association also expanded its operation, building a large tabernacle auditorium and over 200 cottages that could be rented to visitors.

By the late 1800s, Oak Bluffs was attracting thousands of summer tourists each year, arriving on steamships like the Island Home. The port at Oak Bluffs was bustling with activity during the summer months. The town had successfully pivoted from a small fishing and farming community into a fashionable vacation resort.

Religious Camp Meetings

In the mid-19th century, Oak Bluffs became a popular summer destination for religious camp meetings. The first of these gatherings was organized in 1835 by Rev. Phineas Fisk of the Methodist Episcopal Church in New Bedford. Hundreds of Methodists would come to Martha’s Vineyard each summer to camp in tents and participate in revivalist services.

In 1869, the Oak Bluffs Land and Wharf Company began developing the area around Wesleyan Grove into a residential community called “Cottage City.” Simple wood-frame cottages were constructed in close proximity to the open-air tabernacle where the camp meetings took place. Prominent Methodists such as Bishop Gilbert Haven purchased or built summer cottages there. The narrow lanes and small lots gave the community a quaint, idyllic character. By the late 1800s, Oak Bluffs hosted multiple denominational camp meetings each summer.

Cottage City

In the years following the Civil War, Oak Bluffs experienced a tourism boom as steamships began bringing visitors from Boston and New York. By the late 1860s, the community was renamed Cottage City to reflect its burgeoning status as a summer resort town.

Grand cottages in the Carpenter Gothic architectural style began popping up, creating a picturesque neighborhood of gingerbread trimmed houses. These ornate cottages, built around Trinity Park overlooking Nantucket Sound, became the hallmark of Cottage City. Wealthy families from Boston, New York and beyond built summer homes here to escape the heat and congestion of the cities.

Prominent businessman and camp meeting association president Robert F. Madison developed the Oak Bluffs Land and Wharf Company to construct additional cottages and hotels for the influx of tourists. By the late 1870s, over 300 cottages and various inns lined the shores of Cottage City.

The town took on a festive, almost carnival-like atmosphere during the summer months. Steamships brought thousands of day-trippers for seaside excursions, picnic groves and band concerts. The beaches, yacht regattas, dances, and other entertainments solidified Oak Bluffs as a premier New England summer colony.

20th Century

Oak Bluffs continued its development as a popular summer resort town in the 20th century. The town saw steady population growth and expansion of tourist facilities.

New hotels, inns, shops, and restaurants opened up to serve the summer visitors that flocked to Oak Bluffs each year. The town also became known for its gingerbread-trimmed cottages, which became an iconic part of its identity.

Transportation improved with the construction of new roads and the Martha’s Vineyard Airport, allowing more tourists to easily access the island. This further fueled Oak Bluffs’ growth as a vacation destination.

Some of the notable new establishments and attractions built in Oak Bluffs in the 20th century included the Flying Horses Carousel, the Island Inn, the Dockside Inn, Ocean Park, and the Martha’s Vineyard Camp Meeting Association’s Trinity Park.

While tourism drove much of Oak Bluffs’ economy, fishing and boat building also remained important local industries during this time period. The town expanded the harbor and fishing facilities to accommodate commercial fishing fleets.

Overall, the 20th century represented a time of continued prosperity and development for Oak Bluffs as it grew into one of Martha’s Vineyard’s premier resort communities. The town successfully built upon its 19th century foundations as a vacation destination for tourists seeking sun, sand, and leisure.

Famous Visitors

Oak Bluffs has attracted many famous visitors over the years who were drawn to its seaside location and vibrant community. During the late 19th and early 20th century, it became a popular summer vacation spot for presidents and their families.

Ulysses S. Grant visited Oak Bluffs for three summers during his presidency in the 1870s. Rutherford B. Hayes brought his wife Lucy to Oak Bluffs in 1877 during the first summer of his presidency for a “private vacation.”

President Grover Cleveland spent summer vacations in Oak Bluffs during both of his terms in the 1890s. Cleveland’s Secretary of the Navy, William C. Whitney, also had a summer home in Oak Bluffs.

President Benjamin Harrison vacationed in Oak Bluffs with his wife for two weeks in the summer of 1891 during his term. They stayed at the Sea View Hotel.

The most famous presidential visitor was Bill Clinton, who vacationed in Oak Bluffs every summer from 1993 to 2000 during his presidency. The Clintons stayed at the Island Inn and enjoyed spending time relaxing on the town’s beaches.

In addition to presidents, Oak Bluffs hosted many other celebrity visitors. African American intellectual and civil rights activist W.E.B. Du Bois owned a summer home in Oak Bluffs and organized the annual Emancipation Day celebration there. Poet Dorothy West was an acclaimed member of the Harlem Renaissance who grew up and lived in Oak Bluffs. Entertainer Liza Minnelli and her mother, Judy Garland, were among the famous performers who entertained at The Barn, a local music hall.

Over the decades, Oak Bluffs has welcomed presidents, writers, intellectuals, performers, and activists, who were drawn to its vibrant cultural scene and seaside location. The town’s interesting history and architecture continue to attract high-profile visitors today.

Historic Landmarks

Oak Bluffs has several historic landmarks that reflect its unique history as both a religious retreat and a summer resort town. The most iconic landmarks are the ornate Victorian gingerbread cottages that line the streets around Ocean Park. These brightly painted cottages were constructed in the late 19th century during the Cottage City era. The cottages feature decorative trim work, turrets, and porches.

Another key landmark is the Martha’s Vineyard Camp Meeting Association Tabernacle. This large, round open-air structure was built in 1879 and was used for religious services by the Methodists who gathered here. The Tabernacle continues to host programs and events today, including concerts by the Martha’s Vineyard Regional High School Band.

These gingerbread cottages and the Tabernacle give Oak Bluffs a quaint, historic architectural charm that is unique among Vineyard towns. They are treasured local landmarks that provide a window into the Victorian-era origins of Oak Bluffs as both a religious retreat and a fashionable seaside resort.

Oak Bluffs Today

Oak Bluffs is still a popular summer vacation destination today. Tourism remains a major industry, with thousands of visitors flocking to the town each summer to enjoy the beaches, shops, restaurants, and recreational activities.

The town’s vibrant harbor is still central to Oak Bluffs. Commercial fishing boats and ferries operate out of the harbor, connecting the island to mainland Massachusetts. The harbor is lined with seafood restaurants, ice cream shops, bars, and souvenir stores that cater to tourists. Sailing charters, fishing excursions, and harbor cruises also operate out of the harbor during the summer.

In the 21st century, Oak Bluffs has maintained its quaint New England seaside charm while continuing to modernize. Historic inns and hotels have been updated with modern amenities while retaining their Victorian architecture. The town has welcomed new dining and shopping options, while still preserving its walkable downtown of locally-owned businesses.

While Oak Bluffs has changed over the centuries, it remains a beloved summer escape known for its gingerbread cottages, vibrant harbor, carousel, and welcoming community. It continues to honor its history and traditions while evolving to meet the needs of 21st century visitors and residents.




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