1. Things to know about visiting Chilmark
While I was living in NYC, my relatives had a home on Martha's Vineyard. I still love going back and exploring local towns.
Do I have a favorite season to visit? I know you'll think it very specific, but I love the two weeks in November before the crowds arrive for Thanksgiving. The weather is perfect for autumn leaf changing walks. Best of all, in early November, there isn't a soul on the beach!
But Chilmark is a joy to visit year-round. It's known for its family farms, beaches, and scenic cliff views.
One down side here is that accommodations are very pricey. For example, Beach Plum Inn & Restauraunt is a great hotel, but it's $600 per night. Prices don't get much lower in the off season.
For an affordable way to visit, stay in Woods Hole (from $100) and take the car ferry over to Martha's Vineyard first thing in the morning for a day trip. Just make sure you get your ferry reservations well ahead of time.
How to Get to Chilmark
- By Ferry: Take a Steamship Authority ferry from Woods Hole to Vineyard Haven or Oak Bluffs. Then drive or take the bus to Chilmark.
- By Air: Fly into Martha’s Vineyard Airport (MVY). Rent a car at the airport.
- By Car: Cars are allowed on ferries by reservation; island buses also serve Chilmark seasonally.
- Good to know: If you rent a car in lets say Boston, you may need to purchase additional insurance to take the car on the ferry. Just something to ask about when booking your rental!
2. Meet the Animals at Native Earth Teaching Farm
Start your visit at Native Earth Teaching Farm, open seasonally during the warmer months.
You can stroll through the gardens, pet the goats and enjoy nature at your own pace.
You can purchase seasonal produce from the community gardens.
If you are in Chilmark in the off season, you can call them and see if you can visit.
Where you'll find it: 94 N Rd, Chilmark, MA 02535, Phone: 508-645-3304
3. Experience Artistic Expression at The Yard in Chilmark
See a dance show at The Yard.
If you visit from June - September, there are weekly events. In addition to dance shows, you can catch music nights with local musicians, and kids summer programs.
During the summer, you can sign up for community dance and yoga classes every morning in the beautiful open air studio.
Chilmark is a charming, walkable town. The Yard is a quick 3-minute walk from the Chilmark Public Library.
4. Take a tour of The Grey Barn
If you love animals like I do, book a tour at The Grey Barn. It's a small family farm that's home to happy animals. They also make great artisanal cheese.
Tours usually take place in the afternoon. You need to book well ahead of time. Tours are priced from $75 per person.
You can buy handmade organic cheeses and fresh homemade bread. Head to the beach after for a great picnic.
Where You'll Find it: 22 S Rd, Chilmark, MA 02535, Phone: 508-645-4854
5. Grab a Sandwich at the Chilmark General Store
Stop by the Chilmark General Store to grab some sandwiches or pizza slices for your picnic on the beach.
Linger for a minute to soak up the community vibe in this unique small town market. You'll see neighbors meeting for coffee. Bikers that have come in to refuel before hitting the cliffs.
Don't miss a cup of their organic coffee to go!
Where is it: 7 State Rd, Chilmark, MA 02535, Phone: 508-645-3739
Recommended Activities for Families
6. Hike to Sweeping Views at Menemsha Hills
You probably already know that a trip to Menemsha Hills is like walking right onto a set of a dramatic movie.
On most days, I could see Vineyard Sound and the Elizabeth Islands. The cliffs are the result of thousands of years' worth of glacial retreats and advances.
Similar to the rest of Martha’s Vineyard, it is comprised of many different mini environments. You'll woodland groves, coastal plains, and low wetlands.
Menemsha Hills is also home to the 308-foot Prospect Hill. Enjoy the use of many beautiful, marked trails with your family, friends, or your beloved pooch.
7. If You’re Looking for a Quiet Beach Day, Visit Great Rock Bight Preserve
I want to end this post about the best things to do in Chilmark with the best kept secret: Great Rock Bight Preserve.
Follow the trails that wind around and through rolling meadows. Admire refreshing woodlands, and upland ponds. Enjoy the privacy of a windy and picturesque beach.
See famous features of the preserve like the large glacial erratic boulder for which the preserve was named.
8. Take the Kids to the Chilmark Public Library
If you your kids have to catch up on their summer reading, take them to the well-stocked Chilmark Public Library.
Browse a collection of 34,000 items and over 50,000 digital titles.
If you are a history buff, the library was established in 1882 and was the first public library on Martha's Vineyard.
Where to find it: 522 S Rd, Chilmark, MA 02535, Phone: 508-645-3360
Plan Your Trip