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Martha’s Vineyard in May: 14 Enticing Reasons to Visit
Curious about visiting Martha’s Vineyard in May, but wondering what it’s really like before the summer rush?
In May on Martha’s Vineyard, the island starts to wake up, with forsythia and lilacs blooming and local businesses opening their doors, yet it’s not as crowded as the summer months.
Outdoor and sporting events are the theme for this month. It may not be beach weather just yet, but the comfortable weather is ideal for hiking, running, kayaking or renting bikes.
Having visited Martha’s Vineyard in spring, summer, winter and fall, I’ve found the shoulder season to be one of the most rewarding times to explore the island.
From scenic bike rides to Mother’s Day celebrations and tasting the earliest catches of seafood, there are so many reasons to visit at this time of year! Check out this guide to the very best of Martha’s Vineyard in May.
👉 Jump to: Things to Do | Tips for Visiting in May | Getting Here | Hotels open in May | Restaurants | May Weather | What to Wear | FAQ
Things to do in Martha’s Vineyard in May
1. Say hello to summer! Memorial Day weekend on Martha’s Vineyard
🗓️ When: May 23rd- 26th 2025 | 📍 Where: Island-Wide
This is the official start to the summer season on the island and it’s a jam-packed weekend full of restaurant openings, live music, store events, pop up markets and art exhibitions.
Confirmed events so far include the Martha’s Vineyard Environmental film festival (22nd – 25th at the film center) and the opening of the Jaws 50th anniversary exhibition at the MV Museum (24th). The blessing of the fleet takes place at Menemsha Harbor on the 25th.
While 2025 dates are still being announced, some notable events from last year were the weekend parties with live music at Town, Nomans, Black Dog and S+S Kitchenette and the Memorial Day parade in Vineyard Haven.
Watch out for opening-day sales at local stores . This is always a great weekend for shopping on Martha’s Vineyard!
2. Treat your Mama this Mother’s Day
🗓️ When: May 11th 2025 | 📍 Where: Island-wide
Martha’s Vineyard is a great place to celebrate Mother’s Day!
The Harbor View Hotel is offering mini family portrait photo sessions with island photographer David Welch, alongside a delicious brunch at Bettini.
The weekend before Mother’s day, Oak Bluffs Public Library is hosting a free floral arrangement workshop (May 3rd) with the Garden Club of Martha’s Vineyard (registration required). Learn the basics of floral design a take home a beautiful arrangement!
On May 4th, West Tisbury Library is offering free Mother’s Day portrait photographs by Lynn Christoffers in the children’s room. Many of the libraries across the island hold crafting events for kids to make Mother’s Day gifts.
Special brunch menus will also be available at The Pawnee House, Alchemy and S&S Kitchenette.
3. Discover Local Artistry at Vineyard Artisans First Show of the season
🗓️ When: May 24th & 25th 2025 | 📍 Where: Grange Hall, West Tisbury
Mark your calendars for this show of handmade artworks from local Island artists. Enjoy free parking and admission, demonstrations and catered food.
It’s a family-friendly event with a playground for the little ones too. Explore unique creations by local artisans, and take the opportunity to find a special piece of Martha’s Vineyard to take home.
4. Peaceful Retreat at Mytoi Japanese Gardens
🗓️ When: May | 📍 Where: Chappaquiddick Island
Take a ride on the Chappy Ferry to find some serenity at the exquisite Mytoi gardens on Chappaquiddick. This is my happy place off season when there are fewer crowds. Enjoyable for a romantic stroll with your partner, it’s fun for kids too.
Mine love to wander along the winding paths, cross quaint wooden bridges, and maybe spot a frog or fish in the pond. Mytoi showcases a beautiful blend of native and exotic plants at this time of the year.
5. Attend Porchfest in Edgartown
🗓️ When: May 17th 2025 | 📍 Where: Edgartown
A relatively new event on the island, Porchfest first came to Edgartown in 2024. This family-friendly festival brings the community together through music, with local musicians performing on porches around Edgartown.
I’ve been to one of these in Somerville, near Boston and loved the atmosphere, community spirit and opportunity to discover new music. Edgartown is such a great location for a Porchfest!
Porchfest will spread tunes and joy across locations like Rosewater Market, the Hob Knob hotel, Edgartown Books and Nevin Square. As a New England-wide trend, it’s great to see this event will becoming a regular feature in the May calendar.
6. Vineyard Preservation Trust in miniature
🗓️ When: May all month | 📍 Where: The Carnegie, Edgartown
Stop by the Carnegie and see artist Anne Robb’s miniature series of iconic Island landmarks. This special exhibition of Robb’s meticulous craftsmanship is to honor 50 years of preservation efforts by The Vineyard Preservation Trust.
7. Run for a Cause at the Memorial 5K Road Race
🗓️ When: May 25th | 📍 Where: The Town of Oak Bluffs
Lace up for the Hospice of Martha’s Vineyard 5K Road Race. This annual event supports local hospice care and kids can even join in with a 1-mile fun run.
This is a great opportunity to exercise, enjoy the local scenic sights like East Chop Lighthouse and the weather will (hopefully) be ideal for a pleasant run. Plus, your participation helps support the organisations providing essential care for the local community.
8. Take a Beach Stroll
🗓️ When: May | 📍 Where: Island-Wide
If you’ve read any of my other month by month guides to Martha’s Vineyard, you might have noticed I always recommend a trip to the beach, even in the winter! I’m unashamedly biased about my love for the beaches here.
This island has over 100 miles of coastline and a perfect beach for everyone. Catch a sunset, walk your dog, collect shells or visit South Beach for some big surf. If you want to stay dry but enjoy the fresh sea air, take a walk on Lighthouse Beach in downtown Edgartown.
Obviously the beaches can get crowded here in the summer months so I think everyone needs to experience (at least once!) the tranquility of Martha’s Vineyard’s beaches in the quieter seasons
9. Bike the Vineyard Challenge
🗓️ When: May 3rd 2025 | 📍 Where: Start at Martha’s Vineyard High School, Oak Bluffs
On May 3rd, join the Bike MS: Ride the Vineyard event. Choose from routes of 18, 26, or 60 miles, enjoying landmarks like the Gay Head Lighthouse and breathtaking coastal views.
Although the ride takes place on Saturday, this is a good opportunity to spend the entire weekend on the island as there is a welcome event and packet pick-up at Bad Martha’s the night before.
10. Healthy Kids day at the YMCA
🗓️ When: May 10th | 📍 Where: YMCA, Vineyard Haven
The YMCA hosts Healthy Kids day as part of Martha’s Vineyard Screen-free week. This is a free event open to the public. There will be activities like face painting, an obstacle course, toddler zone, snow cones and a pool party!
If your kids love this event, check out YMCA summer camps. You can also ask about short-term membership options if you’re a summer resident or frequent visitor to the island. We always end up heading to the pool here on a rainy day
11. Enjoy a Downtown Shopping Day
🗓️ When: May | 📍 Where: Edgartown, Oak Bluffs, Vineyard Haven
May is an excellent time to browse the boutiques on Martha’s Vineyard. The shops in Edgartown, Oak Bluffs, and Vineyard Haven start to open up with fresh stock for the summer, offering everything from local crafts and homewares to high-end fashion.
This is a great time to support local businesses like Vineyard Vines, Edgartown Books and Rainy Day and find unique items before the tourist rush. Plus, the slightly cooler weather in May makes strolling from shop to shop way more enjoyable than on those sweaty summer days!
12. Go Bananas!
🗓️ When: All month | 📍 Where: West Tisbury
Join the hunt for Hannah’s Bananas at the West Tisbury Library. All month long, you can search for toy bananas hidden around the library. 1 Banana = 1 point. If you have the most points at the end of the month, you will win the grand prize and be crowned Banana Champion!
13. Go on a Quest at the Polly Hill Arboretum
🗓️ When: May 2025 | 📍 Where: West Tisbury
The Arboretum has 20 acres of cultivated grounds and 40 acres of native woodlands for you to explore. In May, they have a packed schedule of events including a class and tour of the early azaleas on the 7th, relaxing forest bathing on the 6th and 20th and a tour of the rhododendron collection on the 14th.
I have really enjoyed visiting the arboretum – it’s a beautiful, peaceful place for a walk. There is always something for the kids too, like the explorers backpacks, quest maps or a woodland gnome hunt!
14. Celebrate 50 years of Morning Glory Farm
🗓️ When: May 1st 2025 | 📍 Where: Edgartown
The banana bread and cookies are some of our favorites from the Morning Glory Farm bakery and the fresh produce is always incredible. Hard to believe the farm is 50 years old! They are celebrating with a party on May 1st.
Between 10.30 and 2pm, you can come by and enjoy a complimentary buffet lunch and snacks from their kitchen and bakery. The first 50 customers will receive a gift bag!
My Insider Tips for Visiting Martha’s Vineyard in May
Plan Ahead for Accommodations and Dining
There’s a surge in weddings in May on the island. You might run into crowds of people having ceremonies or getting pictures taken at locations like the Edgartown Lighthouse or the Harbor View Hotel.
To avoid disappointment, book your stay and dinner reservations well in advance. Ask your hotel if they expect large events or weddings during your stay, especially if you prefer quieter settings.
Opt for Midweek Travel
To escape the weekend crowds and potentially large wedding groups, plan your visit for midweek. You’ll find the island more peaceful and it’s easier to secure reservations at restaurants and hotels.
Consider Different Lodging Options
Instead of large hotels, look into smaller hotels, inns, or vacation rental homes for a more private experience. Vacation rental homes are often available at lower rates than they charge in high season.
Perfect for Couples
May is an excellent time for a romantic getaway, as the island is less popular with families, given that kids are still in school. Enjoy quiet walks on the beach, intimate dinners, and the beautiful spring scenery in a more relaxed atmosphere.
Be Prepared for the Weather
While the weather is generally mild and pleasant in May, it can be unpredictable. Pack layers to accommodate cooler evenings and the occasional rainy day.
How to get to Martha’s Vineyard in May
In May, transport options to the island really start to open up as seasonal ferry routes start operating. You’ll be able to easily get to the island at this time of year.
However, Memorial Day weekend is the kickoff for most seasonal services, so bear this in mind if you are planning on visiting in early May. My guide to visiting in April will give you more detail on transport options before Memorial Day.
Ferry to Martha’s Vineyard in May
The Seastreak from New Bedford sails into Vineyard Haven daily from May 1st to 13th, then switches to Oak Bluffs from the 14th onwards.
The Steamship Authority ferry from Woods Hole sails into Vineyard Haven daily all through May and then adds sailings into Oak Bluffs from the 13th. If you’re coming before Memorial Day – these ferries have the most frequent services.
The Steamship Authority ferry is the only option if you want to bring your car. This route takes 45 minutes, boats run frequently every day and this is my first choice for getting to the island. You can also rent a car on-island or use the bus, Uber, Lyft or taxis to get around Martha’s Vineyard in May.
Advance car reservations are essential but foot passengers don’t need to book in advance.
Seastreak foot passengers should try to book in advance as the boats have a smaller passenger capacity. The trip takes about an hour.
Services starting later in May include the Island Queen from Falmouth to Oak Bluffs. These crossings begin on May 23rd with three crossings daily from Monday to Thursday and five from Friday to Sunday.
The only ferry arriving directly into Edgartown starts service on May 23rd. The Pied Piper (departing from Falmouth) doesn’t run during the week in May, but operates three crossings a day from 23rd to 26th and from 30th to 31st.
The Rhode Island Fast Ferry service begins on May 22nd and operates 2-3 crossings daily from the 22nd to 27th only. The ferry leaves from Quonset Point and arrives in Oak Bluffs.
Fly to Martha’s Vineyard in May
Cape Air flies from regional and large airports in Maine, New Hampshire, New York, Vermont and Massachussetts in May and this is one of the best times to fly to the Vineyard as fares are at their most reasonable.
If you’re near airports like Bar Harbor, Augusta, Rutland, JFK or Logan, now is a good time to check the schedules for a visit in May.
Delta direct flights from New York begin late in May. Jet Blue direct flights from Boston, New York and Washington DC are also available in May. Tradewind daily scheduled flights from New York also being in May. American Airlines services don’t begin until June.
I generally prefer to take the ferry these days because we bring the car and endless luggage now that we have 2 kids and a dog. But if you travel light and it’s just adults in your party, I would definitely recommend the short 19 minute Jet Blue flight from Boston. It’s so easy and convenient!
Martha’s Vineyard Hotels Open in May
Hotel prices are reasonable (by Vineyard standards) in May, especially midweek and some hotels offer great deals and early season discounts. Memorial Day weekend prices are higher than in the earlier part of the month.
- Winnetu Oceanside Resort (opens May 16th)
- Harborview Hotel
- Summercamp
- The Edgar Hotel
- Ashley Inn
- Island Inn
- The Franklin Hotel
- Lambert’s Cove Inn
- The Christopher
- The Sydney
- The Franklin
- Hob Knob
🤩 Search for Martha’s Vineyard Hotels open in May
Restaurants Open on Martha’s Vineyard in May
You’ll have no problem finding places to eat in May on Martha’s Vineyard. The usual year-round favorites like The Wharf, The Barn and Rosewater are always open.
There are also tons of options if you’re looking for your first lobster roll of the season, evening cocktails at a bar or pizza in a beer garden. I’ve listed some of my usual haunts below but keep an eye on local social media accounts for more opening announcements
Edgartown Restaurants
- Alchemy
- Bettini at the Harbor View Hotel
- Bad Martha farmer’s Brewery
- 19 Raw/19 Prime (my favorite date-night restaurant)
- Dock Street Coffee Shop
- Espresso Love (one of my favorites for coffee and lunch, happy customer since 1999)
- Town Bar and Grill
- Cozy Corner Cafe
- Morning Glory Farm Food Truck
- Rosewater Market
- Seafood Shanty (opens mid May)
- Mad Martha’s
Oak Bluffs Restaurants
- Tigerhawk
- Backdoor Donuts
- Fat Ronnies
- The Barn Bowl and Bistro
- Dos Mas Tacos
- The Lookout (huge menu)
- Martha’s Vineyard Chowder Company
- Mo’s Lunch (I love this place! Best sandwiches)
Vineyard Haven Restaurants
- Waterside Market
- The Black Dog Tavern
- The Scottish Bakehouse
- The Net Result
- Art Cliff Diner
- The Attic
- Catboat Coffee Company
Martha’s Vineyard in May: Weather
May in Martha’s Vineyard brings a gentle warmth which I honestly prefer to the heat of the summer. The island shakes off the last chills of winter and average temperatures range between 50°F and 65°F.
You’ll experience a mix of sunny days and occasional spring showers, so the landscape is really pretty, with a mix of vibrant greens and colorful flowers.
This transitional weather is perfect for outdoor activities, like the bike and running events I’ve listed. It’s also ideal for a leisurely stroll along the beach or hiking trails.
What to Wear in Martha’s Vineyard in May
Dressing for May in Martha’s Vineyard calls for versatile layers. Start with comfortable basics like t-shirts or blouses, and add a sweater or light jacket for the cooler mornings and evenings.
Since the weather can swing from sunny to rainy, bring a waterproof jacket or a sturdy umbrella. These are year-round staples on my Martha’s Vineyard packing list to be honest.
Comfortable walking shoes are a must for exploring and don’t forget any specialist gear for running, cycling or water activities if you plan to take part. Pack your sunglasses for bright days and a scarf for breezy evenings by the sea.
Sunscreen and bug spray should round out your list. Ticks are active all year on the Vineyard but I definitely start doing my most thorough checks from spring onwards.
I like to spray all our clothes and walking shoes and socks (especially the kids stuff) with permethrin around this time of year for an extra bit of protection.
Wrap up: Is May on Martha’s Vineyard the Best Time to Visit?
As I wrap up my guide on visiting Martha’s Vineyard in May, you’ll see it’s clear that this time of year has its own unique charm. May offers the opportunity to see the Vineyard in a beautiful state of bloom, away from the peak crowds of July or August.
Enjoy outdoor activities in pleasant weather and participate in unique local events like forest bathing, a road race or cycle through scenic trails. The island in May has something special for everyone.
Share your itinerary and get your questions answered in the Martha’s Vineyard Travel Tips Facebook Group. Take a trip this spring and fall in love with Martha’s Vineyard!
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Frequently Asked Questions about Visiting Martha’s Vineyard in May
Is May a good time to visit Martha’s Vineyard?
Yes, May is a great time to visit Martha’s Vineyard. The island is less crowded, so you’ll have a more relaxed experience. You’ll enjoy the blossoming spring scenery and comfortable temperatures, perfect for outdoor activities.
What is the weather like in Martha’s Vineyard in late May?
In late May, Martha’s Vineyard weather is mild, with average temperatures ranging from 50°F to 65°F. It’s a pleasant time for beach walks and exploring the island.
How many days do you need in Martha’s Vineyard?
To truly appreciate Martha’s Vineyard, plan for at least 3 to 5 days. This gives you enough time to explore the beaches, towns, and local attractions without rushing.
Is it worth it to go to Martha’s Vineyard?
Visiting Martha’s Vineyard is definitely worth it. The island has a unique charm, beautiful landscapes, and a rich history. Whether you’re into nature, food, or culture, there’s something for everyone.
Is Martha’s Vineyard open in May?
Martha’s Vineyard is open in May. It’s the start of the tourist season, so businesses and attractions begin to welcome visitors, making it a good time to experience the island’s offerings.
Is Martha’s Vineyard nice in May?
Yes, Martha’s Vineyard is lovely in May. The island starts to come alive with spring colors and milder weather, ideal for outdoor adventures and experiencing local life without the peak season crowds.
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- Martha’s Vineyard in April: 11 Spring Activities (Best Time to visit!)
- Martha’s Vineyard in August: 13 unmissable summer events
- 5 Awesome Martha’s Vineyard Bus Tours for 2024
- 9 Unmissable Things To Do On Chappaquiddick for a day trip
- 5 Best family restaurants in Martha’s Vineyard for easy dining with kids
