This past week I ventured out to Martha’s Vineyard for the first time ever and wow, what a gorgeous destination! I’ve always been a lover of off-season travel, but especially this year! The streets are a bit quieter, the towns aren’t crowded, and you truly get to experience a place at your own pace. And for me, those advantages to an off-season adventure are priceless. Below I’m sharing all about my October Escape to Martha’s Vineyard. Keep reading to find out how I spent 3 days on the island this fall!
*Please note, we wore masks the entire duration of our trip. The only time we briefly removed our masks were for photos when we were able to ensure we were at a minimum 10+ feet apart from anyone else outdoors. We did not wear masks when we were in our private suite that The Winnetu provided us with. If you have any questions about our Covid-safe travel, please feel free to reach out to me via email. *
[Make sure you keep scrolling so you don’t miss out on the details!]
How To Get There // It’s SO easy to get to Martha’s Vineyard from Fairfield County! As you guys know, I’m at the southern-most part of CT in Greenwich. For me, it’s only a 3 hour drive to New Bedford, MA, which is where I parked my car and hopped on the Seastreak fast ferry to the island!
The ferry ride is an hour long and passengers are required to keep their masks on for the entire duration. I felt comfortable the entire trip, as I was able to sit at least 10 feet away from other passengers.
Where To Stay // I’ll be sharing much more on this later… we stayed at The Winnetu Oceanside Resort in a gorgeous suite overlooking South Beach. The room had its own kitchen, 2 full bathrooms, 2 bedrooms, along with other pull-out sofas/beds.
From the breathtaking ocean views to the attentive and kind staff, The Winnetu really checks off all the boxes! As for amenities, where do I even begin?! Perhaps my favorite amenity was the complimentary shuttle service to and from Edgartown that The Winnetu provides its guests.
Where to Eat // I’ll be sharing more on this below, but for now, here are the places we ate on this trip…
The Dunes (at The Winnetu) // Great for breakfast, a grab & go lunch, & dinner with a stunning sunset view of the ocean
Among The Flowers // Great for breakfast & lunch, either sit outside or grab it & go!
Morning Glory Farm // This gem offers grab & go lunches OR grab some groceries if you’d like to cook for yourself!
The Wharf Pub // Right in the heart of downtown Edgartown, this spot is loved by both locals and tourists!
The Atlantic // Perfect happy hour spot and/or dinner!
The Terrace // A fine-dining establishment featuring classic French cuisine by Chef Patrice Martineau. This isn’t just a luxury dinner, it’s an unforgettable experience.
Things To Do // Let me first say, there is nothing wrong with taking a few days to just relax and soak up the sea breeze and water views. And if that’s what you’re looking for, The Winnetu is the perfect place to do so! If you’re looking for some more action on your trip to Martha’s Vineyard, then rest assured, there is so much to explore year-round! From visiting light houses to shopping fresh fish markets to picking pumpkins, I am certain there is something for everyone.
If you’re looking for effortless luxury paired with priceless views, then look no further than The Winnetu! The Winnetu’s property consists of well-kept grounds, a huge (& heated) pool, plenty of space to roam around, a path that leads you to the beach, and so much more!!
Whether you’re looking for a guest room, a suite, a private cottage, or residence, The Winnetu has something for everyone! We had the opportunity to stay in one of The Winnetu’s 2-bedroom suites with panoramic ocean views. It. Was. Gorgeous. I loved the fact that we had 2 full bathrooms, along with a kitchen, dining space, and living room! The balcony was spacious and offered places to sit and sip your coffee in the morning, and lounge away the afternoon! If it sounds perfect, that’s because it was!
Guests who stay at The Winnetu receive complimentary breakfast each morning, which was delicious! I loved starting my morning off sitting outside, soaking up the ocean views, and enjoying the continental breakfast! If you want to take it back to your room, that’s totally fine too! (We did that one morning and it was so nice to just relax & lounge around in our PJs.)
During our stay we also took advantage of the grab & go lunch offered at the general store (across from the hotel lobby). They had plenty of options from sandwiches to lobster rolls to clam chowder! If you’re looking for something a bit fancier, for dinner you can dine upstairs at The Dunes restaurant. I was very impressed by my beet salad, scallops, and chocolate cake for dessert. (Shhh don’t tell anyone about the cake!)
Moving on to the most important part to any hotel… the staff! I was blown away by how kind and attentive the staff at The Winnetu were. The staff really went above and beyond and it made our stay even more special!
I already mentioned above a few of the places we ate at during our trip, but I wanted to make sure I properly highlighted my favorites!
Let’s start off with Among The Flowers. I was introduced to this gem by my friend Kim of Shorelines Illustrated. This family-owned cafe has been around for over 42 years. They offer outdoor seating that is quite literally among the flowers. I had the veggie wrap and it was delicious! My friends had the quiches and loved those too! (Insider tip: Make sure you get one of their giant chocolate chip cookies!)
Next & not to miss are the grab & go lunch options at Morning Glory Farm. It’s hard to not be happy at this family-owned farm. You’re surrounded by good people doing good for this community & if that doesn’t brighten your day, I’m not sure what will! Their fresh from the farm foods are delicious. If you don’t see something that catches your eye, grab some farm-fresh groceries and make yourself a meal back at The Winnetu!
We ended up making the most epic sunset picnic on the beach with some goodies from Morning Glory Farm. It was just as delicious as it looks, and the company was pretty great too! [cc: @mindybriar, @kristynewengland, @shorelinesillustrated]
Now let’s get fancy… if you’re looking for an unparalleled culinary experience, look no further than The Terrace at The Charlotte Inn. The Terrace isn’t just amazing French cuisine, it’s amazing food surrounded by decor that takes you back to another era. From the telephone booth in the lobby to the letter box by the front door, this place oozes old fashion charm and I loved every ounce of it!
Each dish at The Terrace was incredible. If you told me I’d be fine dining with my friends on Martha’s Vineyard back in March, I wouldn’t have believed you. Yet there I was, enjoying some of the most exquisite French cuisine.
Where do I begin?! For starters I have to give a huge shoutout to Kim Thomas of Shorelines Illustrated. She’s been to Martha’s Vineyard countless times and was able to give us her “must-see” tour of the island in 1 day!
Our tour of the island started with driving out to Aquinnah, located on the western edge of the island. Aquinnah is home to the Gay Head Cliffs and Gay Head Lighthouse. Both are absolutely breathtaking! I couldn’t get over the cliffs diving into the ocean. It’s like nothing I’d ever seen before on the east coast!
Next we drove out to Menemsha, known as a fishing village. Apparently Billy Joel had/has a house out here. How cool!? If you’re looking for fresh-caught fish on the island, this is your place. Perhaps the highlight of the day was spotting a boat named “Helen” in the harbor!
From Menemsha we took our time weaving our way through the island’s countryside. We ended up at Morning Glory Farm, which I’ve already touched upon before. It was such a treat to get to meet Simon, who owns/runs the farm with his family! Simon shared how the farm tackled Covid and thrived during these uncertain times. My favorite story he shared was how they ended up giving out a truck-load of eggs to the local community!
Morning Glory Farm should be on your list to visit year-round, but I especially loved the festive fall pumpkin patch!
After meeting Simon and picking up some groceries, we stopped by Bad Martha’s Brewery in Edgartown to taste their craft beers! They’ve got plenty of outdoor space to spend an afternoon or evening enjoying a flight of their beers. And if you’re hungry, they have a great menu!
From Bad Martha’s we drove back through town and popped out to explore the Edgartown Lighthouse. It was so nice to be able to experience these attractions during the fall season. While I can imagine how the island is equally as amazing during the summer months, I LOVED how quiet & calm it was!
Three days was the perfect amount of time for My October Escape To Martha’s Vineyard! Our first rainy day was quickly overshadowed by two gorgeous sunny days that felt like summer!
If you happen to have a rainy day on your trip to Martha’s Vineyard, I’d suggest taking some time to visit The Carnegie. The Carnegie house, which was the original library on the island, has since been converted into a museum by the Vineyard Trust. The stunning, historic building highlights the island’s history and the living landmarks that The Vineyard Trust has acquired and restored over the years.
I loved being able to walk away from this trip with an appreciation for Martha’s Vineyard’s history, it’s ties to the whaling industry, and for the work that the Vineyard Trust is doing to educate visitors and residents alike.
Have you ever been to Martha’s Vineyard? I’d love to hear about your favorite spots (either in the comments below or send me a DM on Instagram!)
keywords: My October Escape To Martha’s Vineyard // Martha’s Vineyard Fall Travel // Winnetu // Island Escape // Travel Guide // Martha’s Vineyard Travel Guide // New England Travel // Luxury Travel // Getaway // October