If you’re looking for a New England getaway that feels charming without feeling overly planned, put Martha’s Vineyard on your fall list. The key to fully enjoying the island is finding the right home base, giving yourself at least one day to explore and leaving plenty of room to wander. After my family and I visited Martha’s Vineyard, I quickly realized just how much there is to discover beyond the towns most visitors know. From shopping the streets of Edgartown and exploring the colorful cottages of Oak Bluffs to watching the sunset in Menemsha and taking in the Aquinnah Cliffs, here is exactly how I would plan a four day trip to Martha’s Vineyard.

Where To Stay…

When planning a trip to Martha’s Vineyard, choosing the right home base makes all the difference. The island may look small on a map, but having a place that makes it easy to get into town, access the beach, relax between adventures and keep everyone entertained can completely change the experience. For my family, the perfect home base was The Winnetu Oceanside Resort, located in Katama just outside Edgartown.

Why the Winnetu Makes the Perfect Home Base

Set along South Beach, the Winnetu gives you that classic Martha’s Vineyard combination of beach, nature and New England charm, while still being just a short trip from downtown Edgartown. The resort has its own private beach path to South Beach, complimentary transportation into downtown Edgartown and a concierge who can help arrange everything from restaurant reservations to activities around the island.

That combination is what makes it such a great home base. You can spend the morning exploring the island, come back for an afternoon at the resort, then head into Edgartown for dinner without having to pack everyone back into the car.

The accommodations are another reason I would recommend the Winnetu for families. You can choose from studios, suites and cottages, or go bigger with a townhouse, duplex or private home rental. Some of the larger homes offer multiple bedrooms, full kitchens, living spaces, outdoor areas and laundry, giving families the space and flexibility that can make a longer island stay much easier.

Don't Skip the Concierge

One of the things that made our stay so easy was having Neveaha as our concierge. She became our go-to person for everything we wanted to do on the island. She helped us make our dining reservations, arranged a car for us to explore Martha's Vineyard for the day and helped coordinate activities for our kids back at the resort. Before we headed out to explore, she even gave us a detailed map of the island marked with her personal favorite spots, restaurants and recommendations. Having someone who was a native to the island was incredibly helpful, especially because there is so much more to Martha's Vineyard than what you'll find in the main towns. Instead of spending our vacation figuring out where to go and how to get there, we could simply tell Neveaha what we were interested in and she helped us build the day around it. That local knowledge was one of the things that made the Winnetu feel like much more than a place to stay. It gave us a local connection to the island from the moment we arrived.

And then there are the amenities

The Winnetu has two outdoor heated pools, including a main pool with a separate kiddie area and adults-only hot tub, plus a second pool at the Activities Center that is popular for swimming laps. The resort also offers tennis and pickleball, a fitness center, seasonal yoga, Pilates and strength classes, lawn games, a playground, ping-pong, foosball, billiards and life-size chess. There are even antique vehicle rides around Katama, including rides in the Winnetu's vintage vehicles.

For families, I especially love that the resort gives kids plenty to do without requiring you to leave the property every day. During the main season, the Winnetu offers a complimentary Children's Day Program for children ages 3 through 12, along with other family activities. In the fall, programming changes with the season, including a Parent/Toddler program for younger children that can include crafts, open play and outings around Katama and the island.

What I loved most about the Winnetu, was how personal it felt. The resort has a charming, intimate quality that makes you feel less like a hotel guest and more like someone who is genuinely being welcomed back. The staff gets to know you, remembers your family and makes an effort to personalize your stay. From our concierge helping us plan our days to the little touches throughout the resort, that level of personal service made the experience feel incredibly special.

Day 1: Settle In at the Winnetu

After arriving on Martha’s Vineyard, give yourself permission to slow down and enjoy your home base. Spend your first afternoon exploring the grounds, walking the private path to South Beach, letting the kids enjoy the resort and settling into the slower pace of island life.

For families, there is plenty to keep everyone entertained without having to leave the resort. Depending on the season, the resort offers lawn games, a playground, pools and other family activities. One of the kids’ favorites is the daily antique fire truck ride, a fun little Winnetu tradition that gives younger guests a chance to see the property from a completely different perspective.

As the afternoon winds down, head back toward the beach or relax around the resort before dinner. Then end your first night with one of the simplest Winnetu traditions: nightly s’mores around the firepits. It is the kind of activity that makes the first night feel like part of the vacation rather than just the night you arrived.

You don't need to see the island on day one. Settle in, enjoy the resort and let Martha’s Vineyard set the pace.

Day 2: Spend the Day in Edgartown

One of my favorite ways to spend a day on Martha’s Vineyard is to simply wander through Edgartown. From the Winnetu, take the complimentary shuttle into town and spend the day exploring at your own pace. The shuttle makes it easy to enjoy Edgartown without worrying about parking, and fall service is available with a schedule that varies by season.

Start your tour with stopping to get a coffee from Behind the Bookstore, a cozy little spot tucked behind Edgartown Books. It is the perfect place to grab a coffee and a little treat before heading out to explore the town. Don’t forget to stop in the book store as well, this cozy shop is a book lover’s dream!

Walk through the historic downtown streets and along the harbor, then give yourself plenty of time to browse the small shops. Edgartown was my favorite of the island’s towns, and I loved the combination of beautiful historic homes, charming storefronts and that quintessential New England feel. You will get lost in the beauty of the town, I promise!

Make time for an ice cream stop, too. There are a couple of options right in town, including Mad Martha’s and Vineyard Scoops. We tried both, and Vineyard Scoops was our favorite. Ice cream is practically an island staple, and we were very willing participants.

The best part of this day is not having a strict itinerary. Shop, walk along the harbor, pop into a store that catches your eye, stop for ice cream and enjoy the town without rushing from one attraction to the next.

Rather than heading back to the Winnetu for dinner, stay in Edgartown and make your way to Bad Martha Farmer’s Brewery. This was one of our favorite casual stops with the kids. The brewery has a fun, relaxed setting, and our boys especially enjoyed the trivia. We grabbed pizza and pretzels, making it an easy dinner after a full day of exploring. Did I mention the brewery is located inside of a flower nursery!

Once you're finished, take the shuttle back to the Winnetu and call it a night. There is something nice about spending the entire day in one town, especially when you can end the evening with a casual dinner before heading back to your resort.

Day 3: Explore the Island

This is the day I would recommend having a car. During our stay, our concierge arranged a car for us, which gave us the freedom to spend the day exploring the island at our own pace. The island is easy to explore by car, and there is so much to see beyond Edgartown and Oak Bluffs. If a car is not possible, you absolutely can explore the island without one, it just takes a little longer. The Vineyard Transit Authority provides public bus service throughout the island, connecting all six towns. Routes and schedules change with the season, so check the current timetable when planning your trip.

Start in Oak Bluffs

We started our day in Oak Bluffs, one of the island's most recognizable towns. The first stop should be the colorful gingerbread cottages of the Martha's Vineyard Camp Meeting Association. Wander through the neighborhood, take in the intricate details of the cottages and then head into downtown Oak Bluffs to explore the shops and waterfront.

Head Up-Island

From Oak Bluffs, we continued toward West Tisbury, where you get to see a completely different side of Martha's Vineyard. We stopped at Alley's General Store for snacks before continuing to the Field Gallery & Sculpture Garden. We had so much fun posing next to all of the statues. The outdoor sculpture garden is such a unexpected stop, especially if you're traveling with kids. It is an easy place to wander, take photos and spend some time outside without committing to a major attraction.

Visit Island Alpaca

Another unexpected favorite for our family was Island Alpaca. Our boys loved being able to get up close to the alpacas, and the owners shared information about the individual animals and their personalities. It was one of those stops we probably would not have discovered on our own, which is another reason having a knowledgeable concierge can be so helpful.

Finish at the Aquinnah Cliffs

Later in the afternoon, we continued all the way to the opposite side of the island and Aquinnah. Make your way to the cliffs and the Gay Head Lighthouse for what I thought was one of the best views on Martha's Vineyard.

The dramatic cliffs, crashing waves and lighthouse make this a completely different landscape from what you see around Edgartown and Oak Bluffs. It is worth making the drive just to see this side of the island.

If you have enough time, continue toward Menemsha afterward and plan to watch the sunset before heading back to the Winnetu.

This is the day that really showed us how much there is to see beyond the main towns. From the gingerbread cottages of Oak Bluffs to an alpaca farm, a sculpture garden and finally the cliffs of Aquinnah, having a car gave us the flexibility to experience several very different sides of Martha's Vineyard in one day.

Day 4: Slow Down at the Winnetu

Start the morning slowly, then head down the private beach path to South Beach. We grabbed a picnic lunch from the store at the Winnetu and took it down to the beach. We loved how we had the beach all to ourselves. Even though it was a little chilly for our Charleston kids, we loved just sitting and listening to the waves while the kids played in the sand. There was no reservation to make, no schedule to follow and nowhere else we needed to be. Just lunch on the beach and an afternoon enjoying the ocean.

As the afternoon winds down, grab a drink or head to The Dunes for dinner. After dinner take a stroll down to their adirondack chairs by the pond and watch the sunset while the kids play corn hole or kick the ball.

Then finish your final night the same way you started the trip: around the firepit with the Winnetu's nightly s'mores. During the fall, the resort lists nightly s'mores from September 6 through October 19.

After several days of seeing the island, this is the day that reminds you that a Martha's Vineyard getaway doesn't have to be about how much you can fit in. Sometimes the best part is having nowhere else to be.

Martha’s Vineyard Beyond Summer

Martha’s Vineyard doesn’t have to be a summer-only destination. In fact, fall may be one of the best times to experience the island if you want a slower, more relaxed getaway. The crowds begin to thin, the pace feels more laid-back and you can spend your days exploring charming towns, scenic roads and the island’s natural beauty without feeling like you need to fit everything into a summer weekend. There are still plenty of reasons to get outside, from walking the beaches and exploring the villages to enjoying local farms, seasonal events and long dinners. Add in the cooler temperatures, changing foliage and the cozy feeling that comes with being by the ocean in the fall, and Martha’s Vineyard becomes a completely different kind of escape. If you’ve only thought of the Vineyard as a summer destination, I think it’s worth seeing what the island feels like when the season starts to slow down.

Martha’s Vineyard - Your 4 Day Guide