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May Events on the Cape and Islands

Josie Cataldo | 4/26/2022

With spring in full swing and summer right around the corner, it's time to start thinking about all the fun activities and events you're going to enjoy on your Cape Cod vacation! If you're planning on coming to the Cape this May to enjoy a sweet preview of summer, check out our list of seasonal events and activities below!


Celebrate the beautifully vibrant culture and community of Cape Cod by supporting and interacting with the local artists and organizations that will be participating in ArtWeek. Stop by May 1 - May 3 and celebrate the arts and introduce yourself to the Cape creatives that contribute so much to the successes of this special place.

Museum Mondays in May

What better way to start your Cape Cod vacation than by learning about the significant historical events and cultural venues that make this place so special? Take advantage of this extremely generous deal and educate yourself on the history of your favorite vacation destination!

Sandwich Arts and Crafts Fair

Whether you're in the market for beautiful beach jewelry, authentic art pieces to commemorate your Cape Cod vacation, new small business owners to support, or you're just looking to spend the day outside appreciating the creative minds behind craft fairs, the Sandwich Arts and Crafts Fair is an event you're sure to enjoy! The May dates for this events are May 7th and May 28th, so if you're in the area, stop by to shop and show support for the small businesses of Cape Cod!

Hyannis Open Streets on Main Street

Celebrate the start of the summer season on Main Street in Hyannis May 15th! Delicious food, small business shopping, live music, entertaining activities for all ages...what more could you ask for?!

4th Annual Sea Event

A celebration of one of the most exciting treasures you can find on your beach walk... sea glass! This unique sale in Sandwich on May 21st showcases beautifully crafted one-of-a-kind art pieces, sculptures, and souvenirs, and it's definitely an event you won't want to miss!

Walk For Hope

WeNeedaVacation is joining in the march to bring recognition and awareness to one of the most pressing situations on Cape Cod, a shortage of affordable housing. Join us on May 22nd as we walk the town of Orleans to raise funds for our neighbors seeking safety and shelter on Cape Cod.

WeNeedaVacation Ribbon Cutting Ceremony

Come join the WeNeedaVacation team as we celebrate the grand opening of our new office in Orleans followed by an Open House on Sunday, May 29, from 11am to 1pm.

Alex Minasian Quartet Live at the Music Room

Enjoy an evening out on the town and listen to some live music at the Music Room in Yarmouth on May 8th! Celebrate the eccentricity of jazz and appreciate the beauty of music in this intimate environment.

Photo courtesy of The Music Room's website.

6th Annual Spectrum Film Festival

Join the Martha's Vineyard Film Society for their 6th Annual Spectrum Film Festival May 6 - May 8, a 3 day event that promotes productive discussions on LGBTQ+ stories, people, and issues. From guest speakers to film showings to special events, the 6th Annual Spectrum Film Festival is sure to be a great time!

Mother's Day in Edgartown

Take a weekend to celebrate all of the special women in your life by participating in all the fun Mother's Day events in Edgartown! Whether you're sitting back and relaxing in a horse drawn carriage ride or getting your workout in with the Mother's Day 5k, this Mother's Day weekend will be a great way to kick off the spring season and start to summer!

Martha's Vineyard Marathon and Half Marathon

Calling all runners! The Martha's Vineyard Marathon and half Marathon are the perfect way to explore one of the most naturally beautiful landscapes in all of New England! Of course there's going to be quite a bit of training involved, but consider running in either of these races for a new way of exploring one of your favorite vacation destinations!

Nantucket Wine and Food Festival

Indulge in a weekend full of award winning dishes and world class wines at this highly anticipated affair that is one of the most renowned food and wine events in the country!

Celebrate Mother's Day Weekend with 3 Programs Celebrating Mother Nature

Celebrate Mom and Mother Nature Simultaneously by spending Mother's Day Weekend outside! Participate in a variety of events and activities that cater to bird lovers, art lovers, forest fans, and sports fans.

Gifts for Mom | Best Mom Ever Pop Up Shop

On May 7th, show your support for the community and local businesses by shopping small for Mother's Day! Whether you're in the market for homemade candles, beautiful bouquets of flowers, or fresh baked goods, this pop-up has everything you could possibly need to ensure this Mother's Day will be one to remember!

Care for the Cape and Islands Day

Join the community on May 11th to show support for the preservation of the historical former church on Yarmouth Port Common! Celebrate this beautifully vibrant cultural center used for the public's benefit.

Art and Soul Gala

Celebrate the spring and the arts in Sandwich on May 11th at this elegant affair featuring delicious cocktails, a buffet dinner, live jazz, silent auctions, and an art show and sale!

Martha's Vineyard Climate Action Week

Join forces with the Vineyard and take part in a fantastic lineup of events that are helping to make a positive impact/raise awareness when it comes to climate change. Educate yourself on the importance of pressing issues such as warming temperature, rise in sea level, stronger storms, etc., and learn what you can do to help!