How to Spend A Fall Weekend on Martha’s Vineyard

At the end of October I had an awesome opportunity to visit Martha’s Vineyard, Massachusetts. Now, I have never been to Martha’s Vineyard (from hereon referred to sometimes as MV) before; the only knowledge I had of MV was that it is THE summer destination for East Coasters and anyone looking to live the East Coast summer dream. Turns out, MV in the fall is a delightful surprise and should be on everyone’s autumn coastal travel list. The trip was only for a weekend and I decided to go into it blindly with nothing but curiosity and the itinerary that was drawn up by Visit Massachusetts and Visit Martha’s Vineyard tourism board. And let me tell you guys, it was one of the most charming trips I have ever been on! While some shops and restaurants had signs to let guests know they were closed for the season, there was still so much to do on the island. Our trip was sectioned up into three [of six] towns on Martha’s Vineyard: Edgartown, Oaks Bluff, Vineyard Haven. Let’s get into it and get you some inspiration to start planning your fall adventure on Martha’s Vineyard.

dAY 1: Edgartown

Chandler and I decided on two things when we made plans to head to MV: we want to bring our dog Logan and second, we want to bring our car. Getting both over to MV from Boston was incredibly easy thanks to Steamship Authority ferry. With Martha’s Vineyard being about 7 miles off the coast of Massachusetts, you certainly will need to be ferried over. To get to the terminal, it is about an hour and half drive from Boston. Steamship Authority is one of several ferries that operate to take you over to the island and is the only one that ferry over vehicles. You’ll have to make a reservation, have your vehicle information handy and pay a fee for passenger and car. If you’re not bringing over a car, you can make a reservation as well or just walk on for $10 one way and $20 round trip. There are designated parking lots and a shuttle to take you over to the terminal if you will be leaving your car behind. One thing I love about the booking site is if you can’t find the time slot you want, you can waitlist yourself for your preferred time(s) and it’ll automatically book you on it.

It was a 45 minute smooth ferry ride for all, doggy included. About 15 minutes before we were set to arrive, an announcement was made for vehicle owners to get back to their car. Just like driving on to the ferry, getting off was quick and efficient. It was quite the experience. It wasn’t just regular vehicles on that ferry, there were Fedex trucks, UPS trucks, food and beverage delivery trucks, all the trucks.

We arrived to the Woods Hole terminal of Vineyard Haven and headed off to our first stop: Waterside Market. We stopped in for breakfast, I ordered the cinnamon french toast and a black coffee to go which did not disappoint at all.

Then it was off to check into our home away from home in Edgartown, just a 10-15 minute drive. We arrived at the cutest, most tranquil inn: Hob Knob Inn. I’ll let the photos speak for itself:

How cute is this place! It was so cozy and exactly what I imagined staying in an inn would be like. The interior was so home-y and the staff was incredibly kind. It’s pet friendly, the space and our room was very clean; it really did feel like coming home after our long days of exploration. I really can’t recommend the Hob Knob Inn enough.
Being on a bit of a tight schedule, dropped our things off and headed out to explore Edgartown immediately.

My first impression of Edgartown was how stinkin’ (once again) cute! Captain’s cottages, beautiful colors and the main street with shops, decorated for halloween reminded me right away of Halloweentown. I think I could have kept walking around marveling at the homes but we found our way to Sheriff’s Meadow Sanctuary; a public trail right in the middle of Edgartown. Also friendly to pets but they must be leashed, it might have been Logan’s favorite part of the trip. I downloaded the Trails MV app, even though it wasn’t too complicated to navigate I really liked that the app showed us where all the viewpoints were and beautiful they all were. All in one place I got a chance to see so many facets of Martha’s Vineyard’s nature.

I really enjoyed the trail and think this would be a perfect early morning activity. Grab some coffee and take your time to reach each viewpoint and spending some peaceful moments taking in nature.

Before we knew it, it was lunch time and we walked ourselves to Rosewater Market. Located right off of Main Street, it’s a lofty eatery with a really good chicken sandwich. After lunch, Chandler and I dropped Logan back off at the Hob Knob Inn for our next activity: Mytoi Gardens. Located on Chappaquiddick Island you have to take the Chappy Ferry, a three car and passenger ferry, to get on over. During the summer, the line to get on the ferry can stretch on and can be quite the wait. During the fall/winters, it’s not as bad but for us there was still a bit of a wait (~20-30 minutes). Knowing that, we decided to pick up some ice cream from Mad Martha's (it might be the best peppermint ice cream I have ever had) to eat from the car while we waited to get on the ferry.

Once we made it over to Chappaquiddick, or colloquially and affectionately called Chappy, it was a quick arrival to Mytoi. Deciding not to do any research ahead of time I didn’t quite know what to expect and I’m so glad it was a surprise. Mytoi is a beautiful Japanese inspired garden spanning 14 acres. It truly is a gem I never expected to find and experience on Martha’s Vineyard.

It was very tranquil and after spending time with our tour guide learning about all the different plants and trees in the garden, it was time to head back to the hotel.

We relaxed for a bit before getting ready for dinner at Bettini Restaurant in the Harbor View Hotel. Thinking back now, Chandler and I had no idea we were about to have one of the best dining experiences. It was a seriously an iconic meal. From reception to the end, Bettini’s staff crafted a fabulous time for us. I can’t recommend this place enough. It’s a great option for a special occasion or just a treat yourself occasion. It was the perfect dinner to end our first day on Martha’s Vineyard.

Day 2: Oak Bluffs

The next morning while Chandler slept in, I made a quick trip to pick up coffee at Little House Cafe and heading back to Edgartown to enjoy breakfast at the inn. We had a lovely soft, quiet morning and the sun even came out. Of course, we also had something planned for the day, a 3.5 - 4 hour tour of the island with Resort Man. It was dog friendly so Logan also got to come along and learn all about Martha’s Vineyard. Our tour guide and driver Rich was incredibly, incredibly knowledgeable and helped us connect to the island so much! I’ve said it so many times, a walking tour or any sort of city tour is a great addition to the itinerary. The Resort Man tour of the island turned out to be our favorite activity that weekend. The indigenous history of every part of the island is rich and made Martha’s Vineyard even more special. We were able to stop and take pictures. Like here at the Gay Head Cliffs (Aquinnah Cliffs). Look at these gorgeous colorful clay cliffs with the Gay Head Lighthouse perched atop.

We had a lunch stop after the tour but because the tour took a little longer than expected, we made the call to explore Oak Bluffs. There are so many things this town is known for but the thing that popped out to me the most was the home architecture! Lots of gothic, victorian structures and plenty of history including black history. There was a home we drove past that was owned by Joe Overton, possibly the home’s first black owner. While he owned it, it became what was known as the “Summer White house” where black civil rights leader such as Martin Luther King, Jr. and Adam Clayton Powell Jr. visited when they were on the island.

What completely took me by surprise were the gingerbread cottages in the Martha’s Vineyard Campground. Having gone into this trip with absolutely no Googling, I was so amused by this area with all of these cottages arranged just like summer camp cabins.

The history of how these cottages came to be was equally amusing. In 1835, Methodists in the area began setting up tents to attend religious camp meetings and sermons on a half acre land in Oak Bluffs. It was so popular, people from the mainland would also attend and soon there were hundreds of tents set up. Over time, families that came for the services wanted to extend their stay and the tents needed to become much more substantial and voíla, here are the cottages.

No two cottages looked the same and I could have stayed wandering through the campgrounds all day. But we had to get a move on to see more of Oak Bluffs. The next stop was Offshore Ale Company to taste some beers from the island’s first and only brewpub. Since we skipped lunch we ordered the potato pizza to share and it just blew us away. The whole thing would have been devoured if not have for having dinner reservations in a couple of hours. With that being said, I really wanted to chase the light and take some photos of the Edgartown lighthouse as the sun set.

It was just so lovely and what’s more, the manager we met at Bettini recognized Chandler and I and we received such a warm hello.

Dinner called for us to head back to Oak Bluffs to The Pawnee House, a fantastic restaurant with such a great energy. We had excellent time there and I can see this being a great place for a group or date night. Another fantastic dinner to end our night.

Day 3: Vineyard Haven

The weekend had gone by so quickly. Here we were on our last half day on the island, ready to see what Vineyard Haven had in store for us and breakfast at S&S Kitchenette was the first thing. This place was truly a community staple. Everyone that was there to enjoy their morning coffee or breakfast knew the owner. The interior was so cozy and inviting, very “Instagrammable” some would say, especially since the day was a bit rainy. Even in the rain, Vineyard Haven was quite charming. We floated in and out of several shops, taking our time through each one.

We spent the majority of the day at the Martha's Vineyard Museum. Another must do for your MV itinerary, especially if you are a fan of museums and museums that help you feel more connected to the place you’re exploring. There were so many great exhibits like the Jaws exhibit and an exhibit that highlighted the voice of MV’s deaf community. There were ongoing exhibits like one that explores shipping and navigation in Vineyard and Nantucket Sounds including shipwrecks which was very fascinating.

We decided to make a quick trip to Oak Bluffs for lunch at Tigerhawk after the museum. I love a good sandwich and let me tell you, Tigerhawk knows a good sandwich period. There were so many options, I wanted to try them all but narrowed it down to the the fried chicken sandwich Hawk Style and the K-Pop Star sandwich. All the flavors are in these sandwiches. Another amazing find on the island that I wish was in Boston.

With just a few hours before needing to head to the Steamship Authority terminal to go home, we went back to the hotel to pack up and check out. Checking out at Hob Knob Inn was smooth and a little bittersweet, I wasn’t ready to wrap up the perfect, charming weekend. We had one last stop to pick up some dinner at The Attic, which was right on top of Waterside Market, our first stop on Martha’s Vineyard! How very full circle. There were so many great options on the menu but the Short Rib Poutine was the favorite. Soaking in our last bit of time on the island, it suddenly was time to get in line to get on the ferry. A 45 minute ferry ride and a one and half hour drive later, we were back in Boston.

It was such a great weekend that Chandler and I are considering making it an annual fall trip. Martha’s Vineyard just has an incredible rustic charm - we kept being told the island population swells up about 5-7x the population (~20,000) during the peak summer months and while I’m sure it can get very exciting and fun, I much prefer shoulder season travel - as explained in my blog post here. With plenty of activities to do still, a chance to get to explore all the nooks and crannies of the island and see all the vibrant fall colors that, dare I say, was even more prominent on the island than in Boston during this time! Even beaches that are generally reserved in the summer for town residents, are open up to visitors in shoulder season. I would even consider visiting Martha’s Vineyard in the winter, can you imagine how cute the lights would be on those gingerbread cottages?

If you have any questions about getting to the island, what else to do or any questions about the trip - feel free to ask!