There’s something about her that just seems to capture the hearts of those she comes into contact with. With pristine beaches, blue ocean waters, and the breezy salty air to sweep you off your feet, it’s easy to get carried away by the lure and the charm of Martha’s Vineyard and Cape Cod.
One trip, let alone one day, is hardly enough to do it justice, but a short and sweet encounter is better than none at all. Recently, a group of friends and I — mostly hailing from the metro-DC area or further south — hoped to scratch the surface on what the northeast has been keeping secret from us all this time.
Since, A and I are based in Boston, we were the resident “guides” spearheading this trip. Our friends flew from Maryland, Pennsylvania, New York and Virginia and arrived on a Thursday, allowing us a nice long-weekend stretch for maximum adventuring and eats.
Our first full day was dedicated to our daytrip to Martha’s Vineyard. Because our homebase was in Cotuit, it made the most sense for us to drive for the ferry from Woods Hole in Falmouth first thing in the morning by parking our van at the dedicated off-side lot (approximately 4 miles away), and take the shuttle from the lot to the terminal. The ferry ride certainly played a big part in the build up to our vineyard experience. It was so peaceful and so beautiful, and just the perfect distance to enjoy without any fear of motion-sickness (knock on wood).
Once we made it there, it was truly all that I had imagined a quintessential New England small beach town would be. In Oak Bluffs, was our terminal of choice and therefore where we spent our first and last few moments in the island. The area was very walkable and chockfull of surprises. Although there were a handful of businesses closed for the season post-Labor Day, a good bit of seaside activity remained for locals and non-peak season visitors. Edgartown wins the popularity contest for sure, and is home to the Vineyard Vines. However, if you look hard enough and are patient enough, many things lie off the main streets and back roads of these quaint towns. By far the highlight of our trip in my opinion was our pursuit of Bad Martha Beer.
For a day trip, our focus was to enjoy our time together within the three main towns at the tip of the island – Edgartown (our farthest point), Vineyard Haven, and Oak Bluffs. We made sure we had ample time to hit the mandatory sights, such as the Gingerbread Houses/Cottages and Trinity Park Tabernacle, and leisurely stroll around the neighborhoods following our instincts for food and drink stops as well.
As for the remainder of our weekend, we weren’t quite as lucky with the weather, and had to make plans for colder temps. What’s great about Cape Cod and the islands in this case is the multitude of options for groups, couples, families, and adventurers of all comfort levels to create the experience you’re seeking. For equal parts of adventure and solitude, we spent a morning biking along the Cape Cod Rail Trail courtesy of our Dennis Cycle Center rentals. I have not touched a bike in YEARS but they made the process so easy, and the trail right next to the store had a couple of appealing pitstops (hint: one is a winery along the trail!). Well worth the exercise, I tell you.
We of course couldn’t miss an afternoon in the classic town of Chatham for some a lighthouse sighting, beach time, and sunset (or close) cocktails. This vacation life could have lasted forever, in my opinion, but alas we knew it had to end. At least for now.
What’s your must-do/favorite part about Cape Cod and the islands? I have yet to make it to Nantucket so that’s certainly on my list!
I’m sharing our al fresco finds on the trip as well as our quick getaway guide + recommendations based on insight from our Cape Cod-based friends, prior research, and what worked for us on this trip.
Leave me a comment below if you have any questions or check out the Travel + Leisure features on Martha’s Vineyard and Cape Cod, MassVacations.com the Martha’s Vineyard Chamber of Commerce and the Cape Cod Chamber of Commerce websites. Feel free to link up with your post or favorite related links as well!
Thanks for reading!