đ Itinerary: One Perfect Day Up-Island in Chilmark, Aquinnah & West Tisbury (2025)
How to Fit the Best Sights, Seafood, and Views into One Day on Martha's Vineyard
This itinerary will guide you through a thoughtfully planned day in Chilmark, Aquinnah, and West Tisbury, hitting all the must-visit spots while allowing time to relax and take in the scenery. At the end, Iâll share a custom Google Map to help you navigate the itinerary!
â Some Background on Up-Island
âUp-Islandâ refers to the western side of Marthaâs Vineyard, including the towns of Chilmark, Aquinnah, and West Tisbury. Itâs more rural and quiet than the busier Down-Island towns like Edgartown or Oak Bluffsâperfect for those looking to slow down and explore the islandâs natural beauty. Together, these three towns cover roughly half of the islandâs land area but have a much smaller year-round population compared to the busier eastern side.
Up-Island is also home to the Wampanoag Tribe of Gay Head (Aquinnah), who have lived on Marthaâs Vineyard for thousands of years and steward over 500 acres of tribal land. Their deep connection to the land and sea is evident at the Aquinnah Cliffs, a sacred site, and the Aquinnah Cultural Center.
The area is known for its strong farming traditions, with over 30 operational farms across Chilmark, West Tisbury, and Aquinnah. Agriculture remains a cornerstone of the community and is celebrated in many ways.
One Day Up-Island Sample Itinerary
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Morning: Farm Breakfast & Exploration
8:00 AM - Breakfast at The Grey Barn & Farm (Chilmark)
Enjoy a fresh croissant and a cup of Chilmark Coffee at this organic farm and bakery, or grab a loaf of their famous bread to take home. If you have time, join a farm tour to learn about their cheese-making process and regenerative farming practices.
9:30 AM - Explore Polly Hill Arboretum (West Tisbury)
Stroll through native and rare plant collections in this peaceful botanical garden.
Check the schedule for seasonal guided tours or workshops.
đ Mid-Morning: Fishing Villages & Farm Stands
10:45 AM - Visit the West Tisbury Farmerâs Market or Chilmark Flea Market
One of the islandâs best farmerâs markets for fresh produce, handmade goods, and local crafts. Typically the hours are 9a-12p on Wednesdays + Saturdays only (June-October).
Find locally made jewelry, art, and unique gifts at this Chilmark Flea seasonal market, also on Wednesdays and Saturdays but from 9a-2p (June-September)
Alternate Farms to Explore: If you are visiting other days of the week or times of the year, a few notable Farm Stands to stop at are: Beetlebung Farm, North Tabor Farm and Ghost Island Farm - which are typically open year-round.
đ˝ď¸ Afternoon: Coastal Views & Local Eats
12:00 PM - Walk through Menemsha Fishing Village (Chilmark)
Watch fishermen unload their latest catch, take a walk down the beach, and enjoy the mid-day views.
1:00 PM - Lunch at Larsenâs Fish Market
Larsenâs Fish Market â Grab a lobster roll or a cup of chowder and eat right on the docks. Menemsha Fish Market is a great alternative as well with similar offerings.
If youâre looking for non-seafood, stop at The Chilmark General Store on your way up-island for sandwiches and picnic provisions.
2:30 PM - Take a Walk on Philbin Beach (Aquinnah)
This stunning beach is public access with walk-on passes available. You can walk up the beach with views of the historic cliffs and lighthouse.
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Evening: Aquinnahâs Best Views & Dinner with a Sunset
4:00 PM - Visit Gay Head Lighthouse & Aquinnah Cliffs Overlook (Aquinnah)
Take in stunning ocean views from this famous lookout. If the lighthouse is open, you may be able to climb to the top for a panoramic view.
5:30 PM - Dinner at Outermost Inn (Aquinnah)
Enjoy a farm-to-table meal with one of the best sunset views on the island. Itâs seasonal, and reservations are recommended. An alternative option is State Road. Please remember that these locations are beer and wine only, so BYOB if youâd like a cocktail.
7:45 PM - Watch the Sunset
This side if the island is best for sunsets - stay and watch it from Outermost Inn or go back to Menemsha Beach, which is also known for their remarkable sunsets.
đď¸ Optional Beaches & Hikes
If you want to extend your day, here are some great outdoor spots:
Lucy Vincent Beach (Chilmark) â Stunning cliffs, but residents and renters only in summer.
Moshup Beach (Aquinnah) â A short trail leads to this public beach with views of the Aquinnah Cliffs.
Menemsha Hills (Chilmark) â A 3-mile hike with a scenic overlook of Vineyard Sound.
Great Rock Bight Preserve (Chilmark) â A short hike to a secluded beach with a striking boulder formation.
đď¸ Optional Historic & Cultural Stops
For those interested in history and local art, consider these stops:
Vineyard Artisans Fair (West Tisbury) â Held on Sundays & Thursdays 10a-2p, featuring locally made crafts.
Alleyâs General Store (West Tisbury) â The islandâs oldest general store, worth a quick stop.
Field Gallery (West Tisbury) â A unique sculpture garden and art gallery.
Aquinnah Cultural Center (Aquinnah) â Learn about Wampanoag history and heritage.
đ Getting Up-Island: Transportation Tips
Driving: A car is the best way to explore Up-Island since destinations are far apart and sidewalks are limited. Parking is free but fills up fast in summer.
Public Transit: VTA Bus Routes - Buses operate year-round but less frequently in the off-seasonâcheck the schedule before you go.
Route 5: Connects Vineyard Haven/Edgartown to West Tisbury and Chilmark (stops near Alley's General Store)
Route 4: Runs from Chilmark to Aquinnah (stopping at Gay Head Cliffs and local beaches)
Biking Warning đ˛
Not recommended for most visitorsâUp-Island roads are narrow, hilly, and have little to no shoulder.
If biking, take North Road instead of South Road to Menemsha for an easier ride.
đşď¸ Browse MVacayâs Custom Google Map
To help you visualize and orient yourself to the locations in this guide, you can browse the custom Google Map includes all the destinations mentioned!
This itinerary blends scenic spots, local food, and classic Up-Island experiences for a perfect one-day escape to Chilmark, Aquinnah, and West Tisbury.
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