How’d we end up spending a spring weekend in Martha’s Vineyard? The story starts with our honeymoon in Cartagena, Colombia back in 2018. We booked our flights on JetBlue and, after booking, their flight schedules were changed. We ended up spending a night in a Fort Lauderdale airport hotel due to a too-tight connection time and, as an apology, JetBlue gave us credits. Those credits multiplied into more credits following another scheduling issue and, eventually, we found ourselves with several hundred dollars to burn by the end of May 2021.
Adam and I both wanted to book a quick weekend trip somewhere we hadn’t been before and, lucky for us, JetBlue flies direct from Reagan to several spots across New England. We weighed the pros and cons, crowd sourced advice, and ended up deciding that Martha’s Vineyard would be a better option for our first New England beach trip than Nantucket (which, of course, we’re now eager to visit).
Apologies in advance for the photo overload. Turns out Martha’s Vineyard is an incredibly photogenic spot.
Travel Guide: Spring Weekend in Martha’s Vineyard
As two travelers who had never set foot on a New England beach beyond Maine, we had some preconceived ideas of what to expect. Lobsters, chilly evenings, Nantucket reds, hydrangeas, Vineyard Vines, and lots of weathered shingles.
All in all, we weren’t too far off. Martha’s Vineyard is perhaps exactly what you’ve imagined it to be — and that’s exactly why we loved it.
How to Get to Martha’s Vineyard and Get Around
I can only speak to my experience here but, from DC, it’s incredibly quick and easy to get to Martha’s Vineyard, which makes it perfect for a weekend trip. JetBlue flies directly into Martha’s Vineyard from Reagan and, once you’re on the Vineyard, it’s a quick uber ride into your desired town. We left our house at 3:30 PM and were at our hotel by 5:30 PM.
We didn’t rent a car and were totally fine. Friends had recommended we stay in Edgartown so we were able to walk everywhere we wanted to go. The only time we took an uber was to and from the airport. Additionally, we did rent bikes (I’ll get into this later) to tour around the island a bit.
Where to Stay in Martha’s Vineyard
Our hotel was in town in Edgartown, which made it easy to bop around to restaurants and anywhere we needed to go. We booked The Richard Hotel through the Chase Sapphire portal, which allowed us to leverage some of the points we’ve had sitting over the past year and a half.
The hotel itself feels modern and light, but the building dates back several centuries. We stayed in a downstairs room with a private patio that was perfect for enjoying the (free!) breakfast they give you each morning. The outdoor spaces are what truly make this hotel. On our first night, we had cocktails on the front porch before dinner and, on our second, we spent a couple of hours by the fire pit chatting with a couple who was on the last leg of a New England road trip. With perfect spring, summer, and fall temperatures, outdoor spaces are what matter.
And, yes, our room was tiny and expensive, but that’s what you get on the Vineyard. But, as far as locations go, you can’t beat it.
Note: the manager, Julia, was the absolute friendliest woman who gave us so many tips and just made for wonderful conversation each time we came and went.
When to Go for a Spring Weekend in Martha’s Vineyard
We went the week before Memorial Day hoping to catch those days when the days are just slightly warm and the evenings are still chilly, while also beating the high season that comes with June.
What to Pack for a Spring Weekend in Martha’s Vineyard
When we visited in May, the weather was crisp at night and cool to warm during the day. A jean jacket or light sweater and a maxi dress or long pants is perfect for evening, while layering is best during the day. The first day was active and I wore leggings with a t-shirt and a button-down. I was able to take off the button-down when I got warm, but was otherwise comfortable. The second day warmed up significantly and a spring dress was perfect.
The Vineyard can be as dressy or as casual as you prefer. I felt appropriately dressed in a long gingham dress the first night and a jumpsuit with a sweater blazer the second. A casual dress or shorts is perfect for day.
Navigating this Spring Weekend in Martha’s Vineyard Travel Guide
A warning: this is a long one, but you have two options here. You can either read straight through for the day by day, hour by hour Spring Weekend in Martha’s Vineyard itinerary (and, yes, Day Two has twelve stops). Or, you can jump straight to the recommendations by category, where I’ve split them out by where to stay, what to eat, what to do, and given small blurbs for each. Take your pick!
Jump to Recommendations by Category!
Day One
Stop One: Check Into the Hotel and Grab a Cocktail
We arrived at The Richard Hotel just in time for happy hour. We quickly unpacked our bags, freshened up, then settled in for a pre-dinner cocktail on the front porch. It took us approximately thirty seconds to fall in love with Martha’s Vineyard. Driving in, drooling over all the historic homes, I knew this was going to be my kind of place. So, sitting on the front porch, bubbly rosé in hand (even as a non-rosé drinker), I had found my happy place.
Stop Two: Grab a Few More Cocktails at Rosewater Market & Takeaway
One glass of rosé won’t last an evening and, since we hadn’t known what to anticipate in terms of timing, our reservation wasn’t for a few more hours. We walked up to Rosewater Market & Takeway to grab a few drinks to bring back to the hotel. Luckily for us, canned cocktails are all the rage right now, which made it easy to select a few to have on hand for the entire weekend. We headed back to the hotel and, as the temperatures dropped, we migrated from the porch to the fire pit.
Stop Three: Dinner at L’Etoile
We booked dinner at l’etoile, a beloved Martha’s Vineyard staple that’s a favorite of Island families like the Obamas. It was definitely good and the ambiance on the patio was twinkly and romantic, but I do think its reputation is a big part of its allure (or, perhaps, I’d simply had too many drinks too appreciate it — we know I’m usually a one drink and done girl). Regardless, I left full and happy, ready for a good night’s sleep before a busy first fall day.
Day Two
Stop One: Coffee at Espresso Love
I can’t start my day with regular old coffee, so I had to make a stop by Espresso Love, a bustling coffee shop with locations in Boston and Martha’s Vineyard. Be prepared to stand in line and wait, but know they move quickly. With an iced coconut latte in hand, I was ready to hit the road (literally) and perhaps the longest one-day itinerary I’ve ever covered…
Stop Two: Rent Bikes at Wheel Happy Bicycle Shop
We rented bikes from Wheel Happy Bicycle Shop which seemed like a deal at just $30 a day. Given how long we biked, we definitely get our money’s worth. The owner is the friendliest man who patiently figured out the right bike for me while telling us how he’d spent a few summers renting a place on the Vineyard before deciding to move his family there full-time — a tale that certainly got our wheels turning, no pun intended.
Stop Three: Bike to Oak Bluffs
Following the Wheel Happy Bicycle Shop purveyor’s guidance on routes, we set out on our bike to the more touristy town of Oak Bluffs. I’ll preview the day’s itinerary by saying that the first couple of hours were delightful. A breeze was blowing, the sky was cloudy, and there was a pleasant nip in the air. The ride from Edgartown to Oaks Bluff is about thirty minutes, though allow longer because you will definitely want to stop for photos more than once on this adventure.
Once you get to Oaks Bluff, explore the adorable gingerbread cottages that dot the town. It’s like walking through a magical town that’s straight out of a fairy tale. I could have spent hours photographing each and every one.
Stop Four: Break for Back Door Donuts
I tore myself away from the gingerbread cottages for just a few minutes to snag a donut at Back Door Donuts. We kept it classic with the Chocolate Frosted and the Boston Creme.
Stop Five: Take the Long Route Back to Edgartown
Since it was a beautiful day and we were feeling energetic, we didn’t head straight back to Edgartown after touring around Oak Bluffs. Instead, we biked out to Telegraph Hill, a 19th century lighthouse that sits amidst an incredible neighborhood of the most beautiful homes. On our way back through Oak Bluffs, we stumbled upon the Oaks Bluff Arts District, which, while it hadn’t fully opened for the season, did have one gallery welcoming guests. We popped in for a few minutes, chatting with the artist, before heading on our way back to Edgartown.
Stop Six: Stop for Lunch at Lucky Hank’s
At this point, we were several hours into biking and I needed a meal. Donuts and backpack snacks only cut it for so long. We stopped at Lucky Hank’s, a casually charming spot right along the main drag headed into Edgartown. We took a seat on the adorable front patio and placed an order just before they closed up shop for the afternoon. I’d highly recommend both the Vineyard Benedict and the Steak Benedict.
Stop Seven: Take in the Views from the Edgartown Lighthouse
By views, I mean crash a few weddings. The bike ride from town over to the Edgartown Lighthouse is already a delight thanks to the classic New England houses. You’ll find white frame homes with black shutters, weathered shingles, American flags, and hydrangeas and lilac bushes galore. It’s everything you want Martha’s Vineyard to be.
Then, when you arrive at the Edgartown Lighthouse, it gets even better. With the Harbor View Hotel behind you (stop for a drink if you have time!), you’re in prime lighthouse and wedding viewing territory. I counted no less than three wedding photo sessions going on, plus a wedding in progress, as we made our way out to the lighthouse. Yes, the view is incredible, but I also loved peeping on all the happy couples.
Stop Eight: Hop on the Chappy Ferry to Chappaquiddick
Six hours in, we decided our bike ride wasn’t quite over. So, we caught a ride on the Chappy Ferry over to Chappaquiddick. I’ll be honest, at this point, I was exhausted and I could have done without the next two hours. But, alas, we’d committed. The highlight? I snagged this Wes Anderson worthy shot of the Chappaquiddick Beach Club.
Stop Nine: Stroll Around the Mytoi Gardens and Poucha Pond
Since we were already on the island, we decided to follow the path to Mytoi Gardens, a Japanese Garden with a quiet, natural feel. They were still in their off season, but it was a relaxing place to stroll for a half hour or so, and Adam and I both love ornamental Japanese maples, so we were happy to take in the different varieties.
From the gardens, you can make your way to Poucha Pond, the salt marsh, and the sweeping views of the coast. It’s an epic walk out to the water, but well worth it.
Stop Ten: Drop Off the Bikes and Treat Yourself to Ice Cream
After eight hours of biking, I was done. This wasn’t what I’d set out to do, but it was a great way to see a large swath of the island that we may not have otherwise seen had we explored on foot. We were able to easily drop off our bikes after hours and, from there, marched ourselves right over to Mad Martha’s to grab a much needed ice cream cone.
Stop Eleven: Refresh and Relax Back at the Hotel
I needed to sit for a few after all that physical activity and, thankfully, we still had a few cocktails left that we’d picked up at Rosewater the evening before. We got dressed for dinner, staked out our spot on the lounge furniture by the fire pit, and, frankly, I could have stayed right there all night and ordered in had we not already made reservations.
Stop Twelve: Finally, Dinner at Alchemy
Alas, our dinner reservations were calling at a spot that had come highly recommended by more than one person. Even making reservations several weeks out at Alchemy, we were only able to book a late dinner, which is always fine by me when traveling. Now, it’s been a few months and I’m not always wonderful at taking notes on what we got so, beyond the burger, I can’t recall what we had. But, I do remember it was delicious and the atmosphere was bustling. We ran into the owner of the bike shop, speculated on a first date going on next to us, and cheers’d with glasses of champagne on the house — compliments of Adam remembering to tell the hostess that it was our anniversary (which, it was, in fact, our dating anniversary).
Now, an anecdote worth noting. It turns out, when you spend a spring weekend in Martha’s Vineyard, particularly after a pandemic, there are weddings galore. And, on our way home, we stumbled upon more than a few people quite literally stumbling home. While we were entertained by the raucousness of it all, we were informed this is not usually the case on the island. Jury is still out on that one.
Day Two
Stop One: Breakfast at Behind the Bookstore
I expected Martha’s Vineyard to be ridiculously expensive. We went in prepared to spend a lot. But, overall, I was pleasantly surprised to encounter nothing worse than DC prices. Behind the Bookstore is where the sticker shock finally caught up. This spot came so highly recommended by every person I talked to, but, geez, was it pricey. It’s a breakfast spot that doesn’t even list their prices on their website but, if I recall correctly, a bagel and cream cheese was like $7 (to which I said, no, thank you).
We ended up splitting a shakshuka, which was unusual compared to the versions I’ve had, but absolutely delicious. They also left a slightly sour taste in my mouth when I ordered a Shakerado Iced and the barista questioned my ordering it. Yes, I know what it is, and, yes, that’s what I want.
So, would I join the legions of fans? Possibly. I liked the vibe and the food was good. But, the attitude leaves something to be desired.
Stop Two: Shop Around Downtown Edgartown
I don’t think we went home with a single item, but we did spend a couple of hours popping in and out of shops in Edgartown. Since we didn’t buy anything, I didn’t take careful notes and don’t have any specific recommendations, but walk along the downtown and you’re sure to find lots of interesting stores to mill about for an afternoon.
Stop Three: Grab a Beer at Bad Martha Farmer’s Brewery
We actually first tried to go to Bad Martha Farmer’s Brewery after lunch at Lucky Hank’s on our second day but the wait had been too long. Undeterred, we made a reservation to go back on Sunday. We grabbed a seat in the shade and tried tasters of beers while snacking on a pretzel. I’m not sure how COVID precautions are now but, when we went, you did have to stay in your seat and you were required to order food (hence the pretzel). I would 100% recommend a stop here but do make a reservation and be aware that shade is hard to come by.
Stop Four: Enjoy a Drink and the View at Seafood Shanty
With breakfast, browsing, and beer behind us, we were nearing the end of our spring weekend in Martha’s Vineyard. So, we decided to take it in with all its touristy glory. We grabbed a table at the Seafood Shanty, where I won’t even bother to touch on the food because it’s exactly what you’d expect from a restaurant that makes its name based on its location. You don’t come for gourmet dining. You come for sufficient food, cocktails, and fabulous views of the water. With waterside cocktails in hand, we enjoyed incredible vista over the water. Which inspired our next move…
Stop Five: Take in All of Martha’s Vineyard
We wanted to get out on the water…but we only had an hour and a half. So, Adam got creative and asked the water taxi if he could take us around. He wasn’t terribly busy, so we paid him $20 and spent a half hour tooling around, taking in the views of the island from the water. Then, with our feet planted firmly back on dry land, we spent the rest of our time simply walking around admiring the charming homes and plotting next year’s trip back.
Recommendations by Category | Spring Weekend in Martha’s Vineyard
Where to Stay in Martha’s Vineyard
The Richard Hotel: modern, light hotel in a historic building with wonderful outdoor spaces
Where to Eat and Drink in Martha’s Vineyard
Rosewater Market & Takeway: great place to grab to-go drinks and snacks to have on hand at your hotel or for a picnic
l’etoile: elegant spot with seasonal food, a favorite of well-known Vineyard residents
Espresso Love: bustling coffee shop with delicious lattes
Back Door Donuts: donut shop in Oaks Bluffs; don’t miss the Boston Creme
Lucky Hank’s: cute restaurant on outskirts of Edgartown; get the Vineyard Benedict
Mad Martha’s: longstanding Vineyard ice cream shop
Alchemy: sophisticated dining spot; perfect for a weekend date night
Behind the Bookstore: much-recommended breakfast spot; read my itinerary for my thoughts
Bad Martha Farmer’s Brewery: brewery in a garden setting with snacks and beers
Seafood Shanty: touristy spot with great views
What to Do in Martha’s Vineyard
Wheel Happy Bicycle Shop: avoid taking uber by renting bikes to explore the island
Gingerbread Cottages: an easy bike ride from Edgartown to Oak Bluffs takes you to this charming spot
Telegraph Hill: 19th century lighthouse that’s a quick bike ride from Oak Bluffs
Oak Bluffs Arts District: small gathering of art galleries on the edge of town
Edgartown Lighthouse: the iconic Martha’s Vineyard lighthouse
Chappy Ferry: if you’re feeling adventurous, take the ferry over to Chappaquiddick for a long bike ride
Mytoi Gardens: quiet, zen-like Japanese garden on Chappaquiddick
