Planning the Perfect Fall Weekend on Martha’s Vineyard

Photo: Peter Simon

​While many scramble to visit Martha’s Vineyard in the summer, anxious to soak up all the action, there’s a quiet calm that comes over the Island in the fall - secretly making it our favorite time to be here. It’s a sentiment with which many locals agree. On Martha’s Vineyard fall brings a slower pace, cooler (but still beautiful!) weather, great deals and some of the year’s most highly anticipated events. The crowds have lessened making it easier to get around and easing the demand for accommodations. The double benefit for you: lower rates at local hotels and more of the Island to enjoy all to yourself! Following are some insider tips for making the most out of your time during this very special season on Martha’s Vineyard.

Photo: Louisa Gould

​Explore Private Beaches Without Restriction!
During the summer many of the Island’s most coveted beaches are off-limits, being open to residents only. But come mid-September these restrictions are lifted making it possible to explore most Island beaches free of charge and without any special access pass. Dogs are also allowed back on many beaches, meaning you can bring Fido and for a romp on the sand (leashes are still encouraged). Be sure to check out Lambert’s Cove Beach in West Tisbury and Lucy Vincent Beach in Chilmark during the fall, two of the Island’s most beloved beaches where you’re free to roam this time of year. Visit our comprehensive beach map here and plan your stops along the shore. 

Photo: Mila Lowe

​Dine Around Town with Ease
During the summer getting reservations at some of Martha’s Vineyard’s most popular restaurants can be a challenge. Take advantage of the fall when many of the local restaurants are still open and where it’s easier than ever to get a table - maybe even sneak a hello to the chef. Try some of the Island’s newest restaurants like Bettini at the Harbor View Hotel in Edgartown and The Oyster Bar 02557 (from acclaimed chef Ben DeForest of Red Cat Kitchen and Cardboard Box) in Oak Bluffs. Whether it’s seafood, Mexican, Thai or Italian there’s a restaurant waiting for you to explore this fall. Check out our directory of dining options here, and be sure to call ahead as fall hours may be in effect.  

Deals, Deals, Deals
Summer is the most popular time to visit, which also means it’s also the most expensive. Fall brings discounted stays at local hotels and even better deals if you’re willing to travel midweek. Check out our roundup of hot deals at local businesses as well as our last minute lodging specials. If you’re travelling across the water with the Steamship Authority and you’re hoping to bring your car across you’re in luck, fall means it’s easier to get a reservation and, come November, the fares are cheaper too! 

Photo: Max Bossman

​There’s Still a Lot Going On - Get in on the Action!
Any day of the week you can find something new and exciting to do on Martha’s Vineyard, and enjoying Island activities in the fall means parking is easier and crowds have diminished - which means that hiking and biking our trails & paths is great fun, as is hitting the golf courses, whether that be 18-holes, 9-holes, or even a miniature golf course! Major highlights of the fall event calendar include the Martha’s Vineyard Fashion Week September 27 & 28, the Martha’s Vineyard Striped Bass and Bluefish Derby through October 19, Featherstone’s Art of Chocolate Festival October 12 and13, and the Martha’s Vineyard Food & Wine Festival October 23–27. Check out our roundup of fall happenings and browse the local calendar of events for daily things to do during your stay.