Five hours in Oak Bluffs

Let the ferry take its time, then take yours to shop, bike, eat, and think up a next time

Some of these tiny summer cottages built in Oak Bluffs in  the 1860s and ’70s as a Methodist retreat, and now meticulously decorated and maintained, are rented out by their owners.
Some of these tiny summer cottages built in Oak Bluffs in the 1860s and ’70s as a Methodist retreat, and now meticulously decorated and maintained, are rented out by their owners.

We had planned a day trip to Martha’s Vineyard, but it wasn’t in the cards. We were dealt a half day — and we’d make the most of it.

We took a Hy-Line Cruises ferry from Hyannis to Oak Bluffs, and planned to spend the day biking around the whole island. Unfortunately, we didn’t realize the tickets we purchased through LivingSocial were for Hy-Line’s “traditional” ferry — i.e., the slow boat. It took about an hour and 40 minutes to get there (the high-speed ferry takes under an hour) and our return trip was scheduled earlier than we expected. Our slow-motion journey shaved a considerable chunk of time off our day, so we had to scale back our itinerary. Instead of venturing out to explore other parts on the island, we opted to stick around Oak Bluffs and see what the town had to offer.

The answer was: plenty.


Located on the northeast shore, Oak Bluffs has the largest marina on the island and a port that serves as a major entry point for visitors. This seaside resort community separated from Edgartown in 1880, and up until 1907 it was known as “Cottage City.” The town is now home to 5,089 residents, but the summertime population can reach almost 24,000.

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Visiting Oak Bluffs is like stepping back in time. The ferry drops you in a quaint little village. In the center of town stands a big, red, barn-like building with a Victorian-style sign advertising the Flying Horses Carousel (15 Lake Ave. 508-693-9481, www.mvpre, the oldest working merry-go-round in the country. Built in 1876, it was relocated from Coney Island, N.Y., to the Vineyard in 1884, and has been spinning there ever since. The horses have manes and tails made of real horsehair and a Wurlitzer band organ that plays music on paper rolls. It’s one of only a handful of carousels left in the country that still have brass rings for riders to try to grab.

We strolled over to the information booth at the corner of Oak Bluffs and Lake avenues (a junction known as Joseph A. Farland Square — so named in 1962, after a former fire chief) and picked up a free “Historic Walking Tour of Oak Bluffs” booklet that outlines the history of many homes.

The best place for architectural sightseeing is the Martha’s Vineyard Camp Meeting Association (80 Trinity Park, 508-693-0525, www.mvcma
.org). Founded as a Methodist summer retreat in 1835, it contains more than 300 tiny wooden cottages that look like exquisitely-designed dollhouses. Constructed in the 1860s and ’70s, they boast colorful exteriors and ornate gingerbread trim painted in bright hues of purple, pink, yellow, and blue. The cottages are privately owned, but some are available for rent (from $1,300 to $3,000 per week).

Many of these adorable Victorian dwellings are clustered in and around the Tabernacle, an elegant, wrought-iron outdoor cathedral that was built in 1879. On Wednesday evenings in July and August, starting at 8 p.m., the Tabernacle hosts a “community sing” where anyone can join in and sing hymns and folk songs. The biggest event of the summer is the Grand Illumination Night (Aug. 20), when the cottages are decorated with colorful Chinese and Japanese paper lanterns.


We continued to Circuit Avenue, where we browsed in gift shops like The Secret Garden (41 Circuit Ave., 508-693-4759) and Native Spirit (45 Circuit Ave., 508-693-1634), which specializes in Native American goods, including T-shirts and bumper stickers that feature Geronimo, Sitting Bull, and other Native American leaders, along with the slogan, “The Original Chiefs of Homeland Security — Defending Freedom Since 1492.”

For lunch, we went to Nancy’s Restaurant (29 Lake Ave., 508-693-0006,, an Oak Bluffs institution since 1960. We sat outside on the deck overlooking the marina. I feasted on a pan-seared salmon sandwich topped with baby spinach and marinated tomatoes ($15.95) and my travel companion nibbled on a steak tip sandwich ($17.95). We also sipped a drink called “Sunset at Nancy’s,” a deliciously sweet concoction served straight up in a martini glass.

We then hit Kings Rentals (1 Circuit Ave. Extension, 508-693-1887) and paid $29.75 to rent two bicycles for two hours. We rode down Sea View Avenue and passed Ocean Park, a gorgeous expanse of green that’s surrounded by stately Gothic Revival mansions.

Sea View Avenue eventually turns into Beach Road, and goes along Joseph A. Sylvia State Beach (named after a legislator who represented the island from 1936 until the 1960s), a
2-mile public beach that stretches from Oak Bluffs to Edgartown. Parts of the movie “Jaws” were filmed there. There was beautiful scenery everywhere we turned: views of Nantucket Sound on our left, and the salt marshes of Sengekontacket Pond on our right.

We didn’t have time to ride all the way to Edgartown, so we turned around and pedaled back toward Oak Bluffs.


We continued to the other side of the harbor and crossed Washington Park (508-939-1076, www.oakbluffs, where the Oak Bluffs Open Market is held every week. On Sundays, the park is filled with live music and vendors selling locally-grown produce and foods, antiques, and handmade goods — everything from blueberry scones to wampum jewelry to jars of honey.

Our last stop was the Ocean View Restaurant (16 Chapman St., 508-693-2207,, a haven for locals. The no-frills, family-friendly pub has been owned and operated by the same family for more than 30 years, and provides a quiet respite from the busier tourist attractions in downtown. After taking a short break there, we went to return our bikes.

Next time, we’ll take the fast ferry.

Emily Sweeney can be reached at Follow her on Twitter @emilysweeney.