Plan your stay
Chappaquiddick Island
Welcome
Chappaquiddick Island will provide you with an unforgettable vacation! Total privacy, empty beaches, amazing sunrises, stunning sunsets, and total tranquility!
This is your guide to getting the most out of a chappy vacation. Please read it carefully and bookmark it on your devices for easy access during your stay.
Before Arrival
Do your grocery shopping and make any liquor store purchases before taking the little ferry across to Chappaquiddick. Stop and Shop in Edgartown is most convenient, and Al’s Liquor Store is
across the street. Remember to buy or bring your own toiletries. Concierge shopping services are available if you would like the houses stocked and ready for your arrival. Many of the markets will deliver supplies to the Chappy side of the ferry but this will take some coordination to prevent ice cream from melting.
Directions to Chappy
First, you will need to get to Martha's Vineyard Island by boat or by plane.
Your next trip is to get to Chappaquiddick by ferry. If you have a car you will need to get in line for the ferry on Simpsons Lane. There are no reservations and it is first come first served.
Passengers and cyclists can just walk on.
Car Directions
Take Upper Main St
At the flagpole take a left onto Peases Point Way N. and follow the road to the right.
After the park, as you head up a slight hill, take a right onto Simpsons Lane
Now you will probably be in the ferry line. If there is no line (buy a lottery ticket) take a left onto
North Water street and then an immediate right onto Daggett St
Now you are in the last bit of the ferry line.
Turn off you engine while you wait.
Turn off your headlights until you are off the ferry and on the other side. They blind the ferry driver.
Once on Chappy, you will have a short drive over paved and sandy roads to your vacation rental
The Map below shows a path from the Steamship in Vineyard Haven to the airport and then to the Chappy Ferry in Edgartown.
Adjust it as need HOWEVER make sure you go down Simpsons Lane from Pease Point Way. That is the ferry line. Any other way will not put you into the lane.
IMPORTANT - You must take Simpsons Lane to the ferry. Take a left on Peases's Point Way off Main St. just after the flag.
Logistics
First-time visitors to Chappaquiddick Island usually will need some reassurance about being yet another ferry removed from the mainland. Not to worry. You are going to be fine.
First off, the locals call it Chappy. There are about 200 year-round residents of Chappy. In the summer, there are literally thousands of people on the island. All of them get along fine and no one runs out of beer or bbq.
The only way to get to the island most years is by the Chappy ferry. The ferry takes about 1 minute. Two ferries run back and forth simultaneously.
Somethings you should know:
1) Coming from Chappy, you do not have any parking hassles. Parking is free and plentiful.
2) Coming from outside Edgartown, you will have a hard time finding parking anywhere in Edgartown.
3) Going elsewhere on the island, it is easy to hire a Taxi (almost all 15-passenger vans) and then prevent any cops from stopping you for DUI. Uber and Car Services are also available.
4) You can take your car back and forth on the ferry but it is first come first served and you will probably have to wait if you are trying to travel during rush hour. Bring a book or catch up on work and don't be in a hurry.
Maps
Here are directions from the Chappy Ferry Parking Lot to some of our popular vacation rentals, 1 and 37 North Neck.
You can play around with the Chappy map by using these addresses
Ferry lands on the Chappy side near
22 Chappaquiddick Rd, Edgartown, MA 02539
The unique Outermost vacation rental house is located at this address.
Note that Outermost requires a 4WD vehicle.
1 N Neck Rd, Edgartown, MA 02539
Our best chappy vacation rental house is located at this address
37 N Neck Rd, Edgartown, MA 02539
Maps
All of the markets (Edgartown Seafood, Stop & Shop, Edgartown Meat & Fish, Liquor stores, etc.) will deliver food down to the Chappy ferry that you can pick up on the Chappy side.
If you want to do your own shopping, you will need to either take a cab or bring your car over.
From 58 Dock Street (Edgartown Side to the Stop and Shop is a 5-minute drive.
90% of the restaurants are a delightful ten-minute walk from the ferry.
You can play around with the map by using these addresses
Ferry lands on the Edgartown side at Old Sculpin Gallery 58 Dock St, Edgartown, MA 02539
Major shopping Stop & Shop, 245 Upper Main St, Edgartown, MA 02539
FERRY to EDGARTOWN
Crossing on the Chappy ferry as a pedestrian is the best way to enjoy Edgartown, as parking downtown is challenging. There are so many great restaurants there, just book in advance. We have given you some tickets—please leave any remainder in the house for the next guest. The easiest way to do this is for each person to take their ticket to the ferry when they leave the house.
TAKE OUT & CATERING & FOOD
Bill Smith is a good lobster dinner catering service and they are familiar with accessing our property. Edgartown Seafood Market will deliver full lobster dinners to the ferry already prepared or live for your own preparation. You can pick up the delivery on the Chappy side without having to buy a ticket.
Edgartown Meat & Fish Market serves Starbucks coffee, has a sushi & raw bar, gourmet market & deli, prime steaks and seafood; baked goods, and beach basket services. They also sell beer and wine.
Stop & Shop has been enlarged and has a great variety of food
ON CHAPPY
Chappaquiddick has a very nice Community Center (free wifi), left at the end of North Neck and you are there. A tennis & basketball court is
located on the premises. Tennis rackets are in the main house hall closet.
Slip Away Farm, just beyond the community center, sells fresh organic produce.
If you continue straight a mile past the Farm you will come to the beautiful Mytoi Japanese Gardens. Admission is free and the gardens are a lovely retreat and visual indulgence!
Enjoy a picnic on the beach or a refreshing swim in the ocean.
MVOL.com is a great site for MV activities. Pick up the latest guides found at Stop & Shop and businesses. Guided tours are given by the Trustees of Reservations. The Cape Pogue Lighthouse tour is very popular.
Download the TrailsMV app from another great walking trail resource!
Kiteboard lessons are a specialty in
Cape Poge Bay as well as scenic biplane flights out of Katama. Star gazing here is extremely clear and there is a telescope for close-ups on clear nights. Download star gazing apps on your cell phone too.
Will you need a 4WD Car?
Consult your property documentation and manual. Only Outermost House requires 4WD
If you have a vehicle with 4WD and GOOD CLEARANCE AND DEFLATED TIRES
You can stop reading here and move to the next section. If you don't then please read on and don't say we didn't tell you.
Please note: AWD may not get across the beach without getting stuck. Even in sand mode or snow, the tires dig in until the frame is resting on the sand. Heavy vehicles (especially those with many batteries, hybrids, and fully electric vehicles) make the crossing more difficult (please note that a full car of people and food/luggage, etc. is fine.)
Will you make it? It depends on the specific vehicle and beach conditions. While some AWD vehicles can handle sand, especially if it's firm and wet, many struggle with deep, loose sand due to their lower ground clearance and less robust 4WD systems compared to true 4WD vehicles. For a successful AWD beach drive, always lower your tire pressure to around 15-20 PSI, turn off traction control, maintain momentum, and opt for packed or wet sand over soft, dry conditions.
Some AWD vehicles are actually pretty good. It is more important that the tires be deflated to 10 to 20 pounds and that there be good clearance. The sand is very soft and deep, and the road is rutted, so you can scrape the underbody of the vehicle in the sand between the tire ruts.
You will need a vehicle like a Jeep, Land Rover Range Rover, Bronco, Subaru Outback, Chevy Suburburban, Bronco, Toyota 4Runner, Rivian, Mercedes G-Class
Vehicles that are low to the ground with AWD are not recommended, such as Tesla, Audi Quattro, and lower models of Subaru.
Good clearance is more than 9".
Video AWD Tips