Oak Bluffs

Oak Bluffs has unabashedly welcomed summer visitors for over 150 years. It's hard to visit without getting swept up in the resort-town energy.


Oak Bluffs is geographically between the Vineyard’s two other large, prominent harbors. It’s in between them culturally as well. Vineyard Haven, to the north, is more spread out, quieter, and even a little understated. Edgartown, to the south, has more upscale streetscapes and more outscale mansions. All three towns now economically lean on tourism, but only Oak Bluffs has unabashedly welcomed summer visitors for over 150 years.

The marina hosts something like 10,000 transient boats each year, and ferries bring an additional 500,000 individual visitors to town. Closely packed waterfront bars and restaurants hard by the closely packed boats moored to the bulkhead create a dock-and-dine ambience. Day trippers from the Cape in small powerboats conjure memories of frat row. It’s hard to visit Oak Bluffs without getting swept up in the resort-town energy.

Away from the harborfront, though, is a quiet and lovely old town. Along street after street, you’ll find well-kept Victorian cottages with sometimes dramatic polychrome paint schemes that can evoke the “ooooh — aaaah” reaction of a fireworks show. Tight, pretty gardens and a scattering of parks blend easily with the houses.

And the downtown commercial district offers the Vineyard’s best assortment of restaurants — from the harborside umbrella-and-sports bars to plenty of bright, casual, family-friendly options to a handful of spots that are candlelit, locally focused, even idiosyncratic.

📷 Geoff Rand
Many of Oak Bluff’s residential streets feature exuberant, whimsical Victorian architecture.



Oak Bluffs Harbor is the old landlocked Lake Anthony, connected to Nantucket Sound by a channel first dredged around the beginning of the 20th century. About a mile off the entrance is the Squash Meadow, a shoal marked at both ends; otherwise the entrance is clear. In the prevailing southwesterly, the waters outside Oak Bluffs are comfortably in the lee of East Chop. In a strong north or east wind, however, it’s likely to be rough immediately outside the breakwaters and the seas don’t really get tamed until they roll about halfway in.

Fluctuating depths in the entrance channel can sometimes be an issue for long-legged boats. Although it is periodically dredged, the channel is exposed to easterly gales and is subject to nearly incessant ferry traffic. According to the harbormaster’s office, the bottom gets churned around enough that shallow spots develop. The target for dredging has historically been 10 feet at MLLW. In 2011 we saw a minimum of 9 feet on an average low, but in prior years it’s been as shallow as 6.5 feet. The lowest spot is typically right at the mouth of the breakwaters.

Finally, be sure to keep an eye for ferries. The big ones are headed to the terminal outside the harbor. But several come and go through the breakwaters and you’ll want to time your entrance to avoid sharing the channel with them.

Not for navigation


There is no room to anchor inside the breakwater and no protection outside.

Moorings & Slips

Moorings and slips are both handled by the town-owned Oak Bluffs Marina. The 45 moorings are first-come first-served. The 80 slips (mostly tie-ups to the bulkhead running around the harbor perimeter) may be reserved, and generally need to be reserved for summer weekends. Popular weekends can book up before the end of spring. There is a two-night minimum for reservations that include Friday or Saturday.

The small, family-run Dockside Marina just inside the entrance on the left has a handful of slips as well. A member who stayed there on a recent June cruise was impressed by their friendly attitude, and that they answered the phone after 5pm.

We’re impressed that the harbormasters have established an 86 decibel noise limit in the harbor, and we’ve seen them turn boats away whose exhaust was louder.

📷 Geoff Rand
The slips in Oak Bluffs are between pilings. Most boats back in, stern to the bulkhead.


Not for navigation. Charts are not updated. 

Going Ashore

Oak Bluffs’ mid-19th century origins as a Methodist summer camp still exert considerable influence over the town’s appearance. The camp’s early tents were replaced in the 1860s and 70s with closely spaced cottages in the fashion of the time, an ornate gothic-revival style rendered affordably in wood thanks to pattern books, powered saws, and standard building materials. Vineyard carpenters gave their cottages a local flair.

About 300 of the cottages survive within the grounds of the Martha’s Vineyard Campmeeting Association, incorporated “for the purpose of maintaining annual religious meetings. . .” in 1868. Today’s cottage owners and guests continue the Association’s religious and social activities, while observing comprehensive rules to maintain the architecture, along with the community’s traditions. The Association’s buildings were made a National Historic Landmark in 2005.

The other main thread in the town’s development begins in 1866, when the Oak Bluffs Land and Wharf Company purchased land adjacent to the Campmeeting grounds for a secular summer resort. In a twist evocative of Hawthorne, the Methodists immediately erected a picket fence between the sacred and profane, and locked the gate at night. {MVCMA}

The descendants of both 19th century resorts continue to thrive in Oak Bluffs.

📷 Geoff Rand
Oak Bluffs signature “carpenter gothic” cottage architecture dates from its flowering as a summer resort in the latter 19th century.
📷 Geoff Rand
A Vineyard institution.

One Hour Ashore

The essential Oak Bluffs moment is a cocktail and maybe an appetizer in one of the many harborfront eateries. Or cross the street and walk through the residential streets in town.

Off the Beaten Path

The Flying Horses Carousel is “the nation’s oldest operating platform carousel” according to its owners, the Martha’s Vineyard Preservation Trust. It’s been in Oak Bluffs since 1884.

Rainy Day

The Cottage Museum offers a quick glimpse into the origins of Oak Bluffs summer campmeeting culture.

Maritime History

East Chop Lighthouse is about a mile north of the harbor. The Martha’s Vineyard Historical Society offers sunset tours on Sunday evenings.



The marina runs a launch to its moorings when all the slips are full. The charge is per person, per ride.

Dinghy docks are under Nancy’s in the back left corner of the harbor, and in the back right corner, by the showers.

Restrooms and token-operated showers are in a detached building in the back right corner. The Victorian-era Summercamp Hotel (formerly the Wesley Hotel) overlooking the center of the harbor has a boater’s shower package as well. It’s a couple dollars more than the token program, but it gets consistently excellent reviews from crew members.

There are public restrooms at the big ferry terminal just south of the harbor entrance, and in town on Kennebec Street.

Dumpsters intended for use by visiting boats are located all around the harbor.

The Vineyard Transit Authority runs buses around the island on a regular schedule through the summer for something like a dollar a town. The bus stop is across from the big ferry terminal. Or you can rent bikes or scooters at a couple of harborside shops right in Oak Bluffs.

Fitting Out

Diesel is at Church’s Pier, past the Harbormaster/Marina office in the back left corner of the harbor. The fuel dock is run by Jim’s Package Store & Gas Station, just across the street. Staffing can be inconsistent, especially outside July and August; walk over to Jim’s if you need help.

Pumpout and a water hose are free, self-service, and convenient, on a float next to the Marina office.

Ice is at Nancy’s, a restaurant that’s also in the back left corner of the harbor. The freezers are out on the sidewalk and there’s a doorbell to ring for service. The operation may feel a little clandestine but it’s proved friendly and efficient.

There’s a smallish but nicely stocked grocery store right in town on Circuit Street, across the big intersection and then a block or so up from the harbor. A less comprehensive market that also sells beer and wine is in the back right corner of the harbor.

There’s a good hardware store in town as well, that has supplied the clear tape we needed to seal a leaky cabin window.


Oak Bluffs Marina
VHF: 71
Book with Dockwa

Dockside Marina





If you have updated information, corrections, or contributions to this harbor, please share them below. Comments are moderated by Boston Sailing Center. 

Notify of
Inline Feedbacks
View all comments

Oak Bluffs

Navigate your way

Explore More Harbors

Would love your thoughts, please comment.x