Steamship Authority ferry approaching Vineyard Haven, Martha's Vineyard, Massachusetts

It's been a busy summer! My trip to Oak Bluffs on Martha's Vineyard on the last weekend of the summer was a delight. The weather was perfect which was lucky because cooler weather and rain can also occur around this time. Getting a reservation on the Steamship Authority website for traveling with a car two weeks before was not too difficult. The ferries directly into Oak Bluffs were booked up but I was able to get spots on the boats to and from Vineyard Haven.

Left: View of Martha's Vineyard Camp Meeting Association cottages from porch of Summercamp Hotel, Oak Bluffs, Martha's Vineyard, September 2022
Right: Summercamp Hotel (formerly The Wesley Hotel), Lake Ave., Oak Bluffs, September 2022

I stayed at Summercamp Hotel which used to be the Wesley Hotel. It is on the edge of the Martha's Vineyard Camp Meeting Association's gingerbread cottages, and within walking distance to the shops and to Oak Bluffs Town Beach. The large renovated property has fun, colorful decor, and a childhood camp theme throughout the property. Its wide porch looking out on Oak Bluffs Harbor has couches and rocking chairs for relaxing.

I have fond memories of walking around the Martha's Vineyard Cottage Campground in summers past but this was my first time visiting in September. You can avoid the crowds at this time and even up to Columbus Day weekend. However, after Labor Day, some businesses limit hours or close until next summer. The crowds were gone so walking down Circuit Ave. where the shops are located was easy. Visitors were still meandering about but the hustle and bustle of hot July and August days were missing.

Left: South Beach Apparel, 3 Circuit Ave., Oak Bluffs
Right Top: It's Me Clothing and Accessories, 11 Circuit Ave., Oak Bluffs
Right Bottom: Island Novelties, 29 Circuit Ave., Oak Bluffs

During my stay in September, shops were holding end of summer sales. The shops, South Beach Apparel, It's Me, In the Bluff, Island Novelties, Reel Island Co. and Vineyard Vines were offering discounts on sweatshirts, t-shirts, gifts and apparel. For unique artwork, decor and handmade jewelry, Craftworks and Stefanie Wolf Designs were two of my favorites. Shoulder seasons like the time after the peak tourism period can be a great time to visit Scenic Shopping towns.

Left: Craftworks, Circuit Ave., Oak Bluffs, Martha's Vineyard, September 2022
Right: Stefanie Wolf Designs, Circuit Ave., Oak Bluffs, September 2022

There were still many choices for dining although some restaurants had closed for the season. Large portions are served at Jimmy Seas Pan Pasta which is a cozy eatery open for dinner. They have seafood pasta dishes that are big enough for two.

Left: Pan pasta dishes, Vongole in Red Sauce and Scallops Aglio & Olio, at Jimmy Seas, Kennebec Ave., Oak Bluffs, Martha's Vineyard, September 2022
Right: Jimmy Seas Pan Pasta Restaurant, Kennebec Ave., Oak Bluffs, September 2022

The Dockside Marketplace was bustling with outdoor diners, including Nancy's, Coop de Ville, Fishbones and the Sand Bar. The Black Dog Dockside Cafe had coffee, baked goods, and sandwiches to go. Outdoor seating at restaurants, plus public benches along the dock made nice places to sit and watch visitors mill about and boats bob in the harbor.

Left: Oak Bluffs Harbor seen from outdoor seating at Sand Bar and Grill, Dockside Marketplace, Oak Bluffs, Martha's Vineyard, September 2022
Right: View of Oak Bluffs Harbor from Lake Ave., Oak Bluffs, Martha's Vineyard, September 2022

Since I was able to bring my car, I could take a drive southwest on the island out toward the Aquinnah Cliffs. The panoramic views there are spectactular. Tourists flock to the viewing platform for the amazing vistas and photo opportunities. The cafeteria style cafe was closed for renovations, but the small shops perched on this high point were open with limited hours. Handmade artisan jewelry, Vineyard themed decor, casual apparel and souvenirs were on sale in locally owned family businesses.

In the mood for a short hike? There are two walking trails, the South Head Loop toward Moshup Beach, and the North Head loop with views of the Gay Head Lighthouse. There is also the Aquinnah Cultural Center to the left of the parking area. If the weather cooperates, you can easily spend several hours at this spot taking in the natural beauty, shopping, having lunch at the picnic tables, learning about the Wampanoag culture, hiking, and viewing the lighthouse (see lighthouse website for seasonally scheduled lighthouse tours and admission).

Left: Viewing platform at the Aquinnah Cliffs, Martha's Vineyard, September 2022
Right: Gay Head Lighthouse, Aquinnah Cliffs, Martha's Vineyard, September 2022

Aquinnah Cliffs overlooking Vineyard Sound, Aquinnah, Martha's Vineyard

Left Top: Aquinnah Circle Cultural District, Aquinnah Cliffs, Martha's Vineyard
Left Bottom: Stony Creek, decor and gift shop, Aquinnah Cultural District, Aquinnah Cliffs
Right Top: Shops at the Aquinnah Circle Cultural District, Aquinnah Cliffs, Martha's Vineyard
Right Bottom: Hatmarcha Gifts, apparel, jewelry and gift shop in the Aquinnah Cultural District

Southerly views of Moshup Beach and the Atlantic Ocean from the Aquinnah Cliffs

After driving around the western end of Martha's Vineyard, I ended up in Vineyard Haven for the ferry trip home. This presented an opportunity to eat dinner at the Black Dog Tavern on Beach St. Extension, overlooking a small beach and Vineyard Haven Harbor. The old tavern feel and casual window seats inside, plus great food make this my favorite Vineyard Haven restaurant.

Left: Black Dog Wharf and Marina, Beach St. Ext., Vineyard Haven, September 2022
Right: Black Dog Tavern, Beach St. Ext., Vineyard Haven, Martha's Vineyard, September 2022

A Martha's Vineyard day trip or weekend getaway will make you feel like you've really gotten away from it all. Many regular visitors start planning next year's summer trip in the Fall and Winter in order to coordinate with the opening of ferry car reservations for the following year. Plotting my return, I have to wonder if September is my new favorite time to visit.

See our webpage Scenic Shopping Oak Bluffs for trip planning information, photos, and links to shops, restaurants, hotels and activities.