9 Best Things To Do in Martha’s Vineyard in August

August is my favorite time of the year to visit Martha’s Vineyard. It’s the peak of summer, and the island is bustling with energy and excitement.

There are plenty of things to do and see. What I love most about the Vineyard is that there’s something for everyone. Here’s my list of the best things for first-time visitors to do on Martha’s Vineyard during August.

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9 Things to See and Do in Martha’s Vineyard in August for First-Time Visitors

Attend the Martha's Vineyard Agricultural Fair
Explore Edgartown
Go To the Annual Grand Illumination Night
Join the Polar Bear Swimmers
Attend the Martha's Vineyard African-American Film Festival
See the Oak Bluffs Fireworks
Visit the Chilmark Flea Market
Go On the African American Heritage Tour
Rent a Kayak or Paddle board

1. Attend the Martha’s Vineyard Agricultural Fair

This lively four-day agricultural county fair takes place during the 3rd week in August at the Agricultural Hall in West Tisbury (Martha’s Vineyard Agricultural Society).

While there, you can enjoy carnival rides, explore local crafts, indulge in delicious food, and see the livestock shows. It’s a perfect activity for families and people of all ages.

2. Explore Edgartown

If you’re staying in another part of the island, take a stroll through Edgartown, a cute seasonal town with cobblestone streets. Edgartown was once home to the whaling captains, and you’ll notice elegant homes, boutique shops, and a beautiful waterfront.

Before leaving, grab lunch from one of the restaurants along the harbor with gorgeous views. The Seafood Shanty and the Wharf Restaurant & Pub are my favorites, and they’re great if you like seafood.

If you’re venturing to Edgartown for dinner and looking for something upscale, check out Atria. It’s delicious!

3. Go To the Annual Grand Illumination Night

Illumination Night is an island favorite, and occurs every year on the third Wednesday in August from 8:00 to 10:00 p.m. The gingerbread houses in Oak Bluffs are beautifully decorated with thousands of colorful Japanese lanterns.

Owners of the gingerbread houses sit proudly outside while visitors pass by each house admiring the enchanting scene.

While you’re there, enjoy live performances by the Vineyard Haven Band and the community at the Tabernacle. This free event is located at 80 Trinity Park, Oak Bluffs.

Insider Tip: In case it rains, Illumination will be held on Thursday.

4. Join the Polar Bear Swimmers

Every morning, at 7:30 a.m., rain or shine, you can find a group of Black women at Inkwell Beach in Oak Bluffs to swim, exercise, and enjoy their time together. The Polar Bears of Martha’s Vineyard began as a safe space for Black swimmers to build community and thrive.

I’ve ventured to the beach plenty of mornings but have not joined the swimming activities.

Just being there in the morning, taking in the sea air, and seeing women and some men of all ages turn up for this special tradition is a real treat.

If you’re a swimmer and want to start your day with exercise and good vibes, then this is an activity you won’t want to miss!

5. Attend the Martha’s Vineyard African-American Film Festival

The Martha’s Vineyard African American Film Festival (MVAAFF) is a nine-day event where independent and established African-American filmmakers showcase their documentaries and short films from around the world.

The festival kicks off during the first week in August, and screenings are held at the MV Performing Arts Center in Oak Bluffs.

The MVAAF is one of the most anticipated events on the Vineyard, so be sure to check out the website for screening and ticket information.

6. See the Oak Bluffs Fireworks

I always look forward to the annual Oak Bluffs fireworks. They take place on the third Friday in August in Ocean Park. The show begins once it gets dark, around 9 p.m.

To secure a good seat for the fireworks, most people arrive early, set up blankets and chairs, and then return in the early evening with pizza from Giordano’s or pack a picnic dinner and games.

This is a popular activity, so be sure to arrive early. If you’re driving from another part of the island, parking is available at Waban Alley Park and Washington Park. The Oak Bluffs fireworks are a treat and guarantee you’ll have a wonderful time!

7. Visit the Chilmark Flea Market

The Chilmark Flea Market takes place beyond August; it’s held every Wednesday and Saturday at 142 North Road from June until September.

Here, you will find handmade crafts from Vineyard artists, vintage collectibles, and imported items.
The Chilmark Flea Market has been around for 50 years and is a great way to see another part of the island. It offers free parking and admission.

Dark T-shirt with native Americans on the front of Mt. Rushmore with the words: The Original Founding Fathers at Chilmark fair in Martha's Vineyard.

8. Go On the African American Heritage Tour

The African-American Heritage Trail of Martha’s Vineyard offers walking tours in Oak Bluffs and Edgartown and an all-island driving tour, including a stop at the Aquinnah Cliffs.
On the tours, you’ll learn about the history and contributions of African Americans to the island and hear from your guide about their deep connections with the Wampanoag Tribe.
I went on the all-island driving tour and learned so much about the island’s rich culture and the essential relationships between the African American people and the Wampanoag Tribe.
This informative and engaging tour deepened my connection to the island’s rich history.

Bronze plaque along cement wall in Martha's Vineyard.

Gold plaque on mounted on the side of a red building.

9. Rent a Kayak or Paddle board

Martha’s Vineyard is known for its natural beauty, and with that comes plenty of outdoor activities. One of my personal favorites is kayaking or paddle boarding. Sengekontacket Pond is a popular spot because the waters are calm.

The best time for kayaking is either first thing in the morning or during the sunset. Island Spirt Kayak accommodates all levels if you’re a first-timer looking for a new adventure.

Yellow and red kayak in a pond overlooking the sunset.

Conclusion – Lady Chin’s Two Cents

Visiting Martha’s Vineyard in August has become a tradition for me. While I feel there’s never a wrong time to visit the island, I always look forward to August because it means going on new adventures and re-experiencing the island favorites that bring me back to my childhood.

It’s a chance for first-time visitors to unplug and experience the island’s unique charm and beauty. You might become a vineyard lifer like me—it only takes one visit!