As many New Englanders know, Martha’s Vineyard is a hot summer destination as soon as the summer months arrive each year. The beaches are stunning, the restaurants and shops are bustling and the laid back island vibe is sure to put you in a feel good mood. I’ve been able to visit the Vineyard a hand full of times since moving to the Northeast- but admittedly they have always been during the summer months. So when I was asked to visit the Winnetu Oceanside Resort this October and share a “Fall guide to the Vineyard”, I was super excited to learn what the island was in fact like during a different season…and I was really excited to see what it was like without the crowds.
I was lucky enough to visit the island with my friends, Kristy of Kristy and New England , Helen of Style Inherited and Kim of Shoreline Illustrated for a fun girls getaway on one amazing island.
I’m also excited to share that the Winnetu Oceanside Resort has extended their fall season and is remaining open until November 1st! Right now, they are offering three nights for the price of two over the remaining weekends in October – you can learn more about this amazing offering here!
How we got there
I am based along the shoreline in the middle of Connecticut, so from the Fairfield County area to New Bedford, MA it takes about 2.5-3 hours.
From here you will need to hop on a ferry to get to the island. There is also flights on to the island If you want to travel direct, but I will say that the ferry is so easy to travel on that I would recommend this first. You have a few ferry service options for the island -one of my favorites is SeaSteak Ferries in New Bedford MA, They also have NYC and NJ locations if you are closer to the city! The ferry ride is about one hour and will get you to either Vineyard Haven or Oak Bluffs where you can either get a shuttle to the hotel or a taxi. You can also rent a car for your stay or bring your own car. For this trip we used The Winnetu shuttle as well as rented a car for one day of exploring the island,
The Winnetu is named a top 25 New England Resort by Conde Nast Traveler – needless to stay it truly is an unforgettable experience staying at this hotel.
One thing that I love about this hotel is that it is outdoor/indoors throughout the hotel. The doors are all open and you can feel the fresh ocean air flow through each space. One of the prettiest things you will see is the grand entrance! Next to it, you will find a super tasty market and giftshop. I had a deli sandwich and salad from here that was delish!
The lobby is light-filled and super relaxing as soon as you step into the space. You will be greeted by a friendly staff member and then see some great spots to relax and read a book, newspaper or enjoy the warmth of the fire. They also have a lot of games for you to choose from that you are allowed to bring back to your room!
Be sure and check the front desk for the activity schedule! They have daily activities for guests and families to participate in. A few favorites were the Hot Apple Cider and Chocolate Chip cookies as well as the S’mores Station!
You can find this cute American Flag sweater over at J. Alden Clothiers in Essex, Connecticut! If you aren’t in CT, here it is on their website!
We stayed in the Edgartown Two-Bedroom Premium Suite with an Ocean View. I can’t tell you how perfect this suite was for a girls trip or a family trip! It was roomy, well designed and It had some pretty incredible views of the ocean! Our room also had two good size bathrooms, a washer and dryer as well as a full kitchenette with full size fridge.
The bedrooms at The Winnetu are modern and spacious with the softest bedding and sheets. I loved the big soaking tub in the master bathroom – I took full advantage of this one evening after a rainy day in town! The bath helped warm me right up.
I’ve been living in this cozy fall wrap from Foxcroft! You can style it several different ways and it’s just perfect for the season. You can find it here! Be sure and use my code “MINDYFOX” for 20% off your order which is available for a limited time!
The bedrooms were beautifully decorated and a good size. The master had a gorgeous view of the grounds and ocean and even a patio for you to sit outside on and drink your morning coffee.
The hotel also has an amazing pool area as well as family friendly outdoor activities such as the giant chess board and chairs as well as the massive lawn just waiting for your kids to run around on!
This shirt is another one of my favorites. It’s lightweight and you can dress it up or down with some jeans or tuck it into a cute skirt and add a jacket and scarf for some layers! It has a really cute ruffle color and It also is non-iron and has the perfect amount of stretch. Use the code “MINDYFOX” for 20% off your order which is available for a limited time! You can find this shirt here!
Dining at The Dunes…
The Dunes at the Winnetu is a beautiful restaurant at the hotel with incredible food. We had several breakfasts here and a delicious dinner and cocktails. I love the interiors and aesthetic of this space – it’s worth the drive to come visit! It even has a beautiful rooftop patio!
Things to do
Take a Drive and sightsee…
Taking a drive around Martha’s was an incredible way to see the island. You can either rent a car, bring your own, or do a sightseeing tour!
Aquinnah Cliffs and Gay Head Light
You can find this cute zippered tote here!
Head to Aquinnah and visit the beautiful Gay Head Lighthouse and Aquinnah Cliffs Overlook! They are within walking distance from each other and both have stunning views of the Atlantic ocean and cliffs. The water is so blue against the white sand of the cliffs- you will be mesmerized!
Visit the historic fishing village of Menemsha…
Be transported through time as you visit a historic working fishing village in Menemsha! They have several fish markets for you to shop through and so many picturesque spots to snap pics. Be sure and head to Larsen’s Fish Market for some fresh lobster!
You can find this cute striped sweater here!
Immerse yourself in Fall at Morning Glory Farm…
A must-do on your trip is Morning Glory Farm in Edgartown. This beautiful farm was started by The Athearn family in 1975. They have 65 acres of farmland that grows fruits, veggies, and flowers. We had the pleasure of meeting Simon – the Chief of Operations who shared a bit about the farm’s history. It truly is a family run business and one thing is for sure is that it is full of heart and love for the Vineyard and their clients. Their market is filled with brightly colored fruits and veggies and there are lots of grocery items for you to shop through. Be sure and try the Morning Glory muffin – it was to die for!!
Beer lover? Head over to Bad Martha for a flight…
Bad Martha is based in Edgartown and is the home of Bad Martha Brewing Company. It’s a perfect stop in between your excursion or to end the day! They have amazing pizzas and charcuteries as well as delicious handcrafted beer. We tried a couple of flights and paired it with a tasty charcuterie board. I also really loved the rustic aesthetic of the brewery and large outdoor seating area to hang out with your friends.
Say hello, to Edgartown and the Edgartown Harbor Light…
A short stroll through some of the old captain’s houses in Edgartown will lead you to the Edgartown Harbor Light. This lighthouse is a classic white and so idyllic with the tall grass surrounding it and the ocean behind it. It has a lovely walking path to get to it from the road so be sure and have some shoes you don’t mind getting in the sand!
On your walk back to Edgartown, be sure, and take your time looking through all of the charming details of the historic colonials that line the streets! Even in the fall – the flowers were still in bloom (minus the hydrangea- though still beautiful!) and there was lots of festive fall decor.
Once you have arrived in Edgartown be sure and check out the cute local shops! Their are so many fun ones to meander through.
Learn the history of Martha’s Vineyard at a local Museum…
The Carnegie: This beautiful museum is located in Edgartown and is ran by the Vineyard Trust. They had two stunning reading rooms and two stories worth of beautiful exhibits and artifacts that teach you about the history of Edgartown and Martha’s Vineyard. This museum was perfect for a rainy day or if you’re a history buff like me!
Martha’s Vineyard Museum: This museum is located in Vineyard Haven and looks amazing! I didn’t have the time to go on this trip – but I do hope to visit next time!
Enjoy sunset at the beach…
Bring a sweater and a blanket to curl up with your loved ones to enjoy a breathtaking sunset at Katama beach outside of the Winnetu. We brought some wine and cheese with us for this and it made the experience all the more fun!
Where to dine…
There are so many great spots to dine on the Vineyard. A few of my favorites are the following:
The Dunes at the Winnetu: The food and ambiance at the Dunes is exactly what you would hope for when visiting the Vineyard. Classic style, with maritime decor, amazing food, and great service.
Among the Flowers – The perfect natural spot to grab brunch! They have a beautiful selection of breakfast foods and sandwiches. I will definitely be going back here!
Morning Glory Farm: The perfect natural spot to grab cheeses/meats/salads and bakery goods.
The Terrace: Set in the beautiful historic Charlotte Inn- the Terrace is the perfect spot for fine dining at it’s best.
The Atlantic : We had some great cocktails and dinner here – they also have a beautiful outdoor patio by the water!
Ahhhh Martha’s Vineyard, I will be dreaming about you…It was such a memorable and fun trip with the girls! I can’t wait to return and I can’t recommend visiting in the offseason enough.
A big thank you to the Winnetu for hosting our amazing stay and Kim of Shoreline Illustrated for giving us an epic tour of the island.
Thanks for reading and wishing you a very happy fall season!