Insider's Guide to Martha's Vineyard Towns: Oak Bluffs to Edgartown

Oak Bluffs immediately announces itself as different from the rest of the island. While other Vineyard towns embrace understated New England elegance, Oak Bluffs revels in its Victorian exuberance and carnival atmosphere. The town's gingerbread cottages in the Martha's Vineyard Camp Meeting Association (affectionately known as the Campground) represent one of America's most unique architectural collections. These candy-colored cottages originated as simple Methodist camp tents before evolving into the ornate structures we see today.

During my first visit with my grandfather, we spent hours wandering these narrow lanes, him recounting architectural details from his art history background while I documented everything with my travel camera. The Flying Horses Carousel, the nation's oldest operating platform carousel (dating to 1876), remains a highlight for families with young children. My advice? Visit early in the morning before lines form.

For culinary history enthusiasts, Oak Bluffs offers fascinating insights into the island's African American heritage. I highly recommend booking a walking tour that explores this history, followed by lunch at Slice of Life, where their clam chowder rivals any I've tasted across New England. In the evenings, Oak Bluffs Harbor comes alive with families strolling the docks, watching boats return, and enjoying casual seafood dinners at Nancy's Restaurant (their fried clams are exceptional).

The town beach, while not as pristine as others on the island, offers the convenience of proximity to ice cream shops, restrooms, and the essential amenities that make beach days with children manageable.

If Oak Bluffs represents Martha's Vineyard's playful spirit, Edgartown embodies its refined soul. The town's pristine white Greek Revival captain's homes, immaculately maintained gardens, and cobblestone streets speak to its wealthy whaling history. Walking these streets with my grandfather, he would point out architectural details I might have missed—widow's walks, captain's porches, and the subtle differences in colonial design that tell stories of the families who built them.

Edgartown's harbor presents a different atmosphere than Oak Bluffs—less carnival, more yachting club. For families, I recommend taking the short On Time Ferry to Chappaquiddick Island (affectionately called 'Chappy' by locals). The brief crossing delights children, and the island offers secluded beaches and the natural wonder of Cape Poge Wildlife Refuge. Consider booking a tour with a naturalist guide who can explain the delicate ecosystem to children in engaging ways.

Culinary experiences in Edgartown tend toward the upscale, but several establishments welcome families while maintaining the town's refined character. The Port Hunter offers sophisticated seafood in a setting where children are welcomed, not merely tolerated. For a special family dinner, book well in advance at l'étoile, where Chef Michael Brisson creates exceptional French-inspired dishes using island ingredients.

Edgartown's beaches require transportation but reward the effort. South Beach (officially called Katama Beach) offers three miles of pristine Atlantic oceanfront. The waves can be substantial, so families with young children should stay in the guarded areas. I always pack a beach tent for shade and wind protection, essential for making a day at South Beach comfortable with children.

Often overlooked by luxury travelers in favor of its more famous neighbors, Vineyard Haven (officially Tisbury) offers an authentic glimpse into year-round island life. While Oak Bluffs hibernates in winter and Edgartown grows quiet, Vineyard Haven remains the island's working heart through all seasons.

My grandfather particularly appreciated this town's unpretentious character, noting how it balanced tourism needs with practical services for residents. Main Street combines practical shops with unique boutiques like Bunch of Grapes Bookstore—an independent bookseller with an excellent children's section and regular author events during summer. I always recommend families stop here to select island-themed books that can be read during beach days.

Vineyard Haven's cultural highlight is the Martha's Vineyard Playhouse, which offers excellent children's programming throughout summer. Their outdoor performances in the amphitheater are particularly magical for families with children old enough to appreciate live theater under the stars.

The town's culinary scene emphasizes casual, quality dining. For breakfast, try Black Dog Bakery (not the overcrowded café) for morning pastries. The Net Result fish market offers the island's freshest seafood for families staying in accommodations with kitchens. My grandfather taught me to appreciate how fish markets reveal a destination's true relationship with the sea, and The Net Result exemplifies the island's genuine connection to maritime traditions.

Vineyard Haven's Owen Park Beach provides a small, protected swimming area perfect for families with young children. The gentle harbor waters and proximity to town make it ideal for a quick morning swim before the day's activities or a sunset picnic. I recommend packing a insulated cooler backpack for beach picnics—it keeps provisions cold while freeing hands for carrying beach gear and managing children.

While the main towns attract most visitors, Martha's Vineyard's up-island communities offer experiences that feel removed from the summer crowds. During my second visit to the island, I ventured further afield, discovering the quiet charms of these less-trafficked areas.

Menemsha, a tiny fishing village in the township of Chilmark, presents what many consider the quintessential Vineyard experience. This working harbor remains refreshingly uncommercial despite its fame as the filming location for 'Jaws.' The fish markets here—Larsen's and Menemsha Fish Market—offer seafood directly from the boats visible through the window. I recommend purchasing lobsters to cook at your accommodation or, for a simpler option, getting takeout to enjoy on the beach at sunset.

Menemsha Beach provides what is widely regarded as Martha's Vineyard's most spectacular sunset view. Unlike other island beaches, parking is free but limited. Arrive at least two hours before sunset to secure a spot during peak season. The tradition here is to bring dinner, drinks, and chairs to watch the sun sink into the ocean, often accompanied by applause from gathered onlookers when the final sliver disappears.

For families seeking a more adventurous beach experience, Chilmark's Lucy Vincent Beach offers dramatic cliffs and interesting rock formations. Note that access requires staying in Chilmark or obtaining a town beach permit. The effort to reach this beach rewards visitors with significantly smaller crowds and natural beauty that my grandfather described as "reminiscent of certain Portuguese coastal areas, but with New England character."

These up-island areas also offer the island's most spectacular hiking. The Menemsha Hills Reservation provides trails suitable for families with older children, culminating in breathtaking ocean views. I always bring my hiking backpack loaded with water, snacks, and my camera equipment—essential for capturing the dramatic landscapes and keeping everyone comfortable on these trails.

Martha's Vineyard's food scene reflects its maritime heritage, agricultural traditions, and diverse cultural influences—aspects that particularly fascinate me as someone interested in culinary history. While many visitors focus solely on seafood (which is exceptional), the island offers much more for food-curious families.

The Wampanoag tribe's influence on island cuisine remains evident in the preparation of local shellfish and the use of native berries and plants. During summer, seek out opportunities to learn about these traditions through cultural programs at the Aquinnah Cultural Center. These educational experiences provide children with a deeper understanding of the island's first inhabitants and their sustainable food practices.

Martha's Vineyard's agricultural heritage thrives at the island's farms. Morning Glory Farm in Edgartown offers an ideal family experience—children can see where food grows while parents select incredible fresh produce, baked goods, and prepared foods for beach picnics. The farm's cookbook makes an excellent souvenir for those wanting to recreate island flavors at home.

For a special family experience that combines culinary education with entertainment, book a class at Farm.Field.Sea. Their family cooking workshops use island ingredients while teaching sustainable food practices. My grandfather and I participated in their seafood workshop during our trip, an experience that created lasting memories as we learned traditional New England cooking techniques together.

Don't overlook the island's Portuguese influence, a legacy of Azorean sailors who settled here during whaling days. The Portuguese bakery in Vineyard Haven serves malasadas (Portuguese donuts) worth the morning line. This cultural fusion exemplifies how island cuisines evolve through immigration patterns—a topic my grandfather often explored in his academic work.

For families staying in accommodations with kitchens, I recommend investing in a quality seafood preparation kit. Preparing locally caught seafood in your rental creates both a memorable family activity and a more economical approach to enjoying the island's bounty.