Thousands of visitors flock to Martha’s Vineyard to soak up those leisurely summer beach days by the seashore, but the Island stays very much awake and vibrant throughout the fall too. Locals love the cooler temperatures and smaller crowds, and the slower tempo makes for more relaxing days to enjoy the Island’s most coveted areas and events.
Here are 20 tempting reasons to fall for Fall on Martha’s Vineyard, and 20 reasons you’ll want to plan a trip before another season passes you by!
1. Saturday, September 7, 10:30am–5pm: Martha’s Vineyard Wind Festival Attention kite lovers of all ages! Come see kites of all shapes and sizes soar above the gazebo at Ocean Park in Oak Bluffs. Activities include kite making and model sailboat racing for children, and kite flying and frisbee games for young and old. Rain date September 8.
2. Saturday, September 14, 10am–6pm: Tivoli Day
This end-of-summer celebration has been going on for decades and is the place to score a good deal on a locally made product or Martha’s Vineyard souvenir. The event takes place on Circuit Avenue in Oak Bluffs, which is closed to cars for the day, as vendors line the streets with their wares, musicians perform, and attendees savor their last taste of summer.
3. Sunday, September 15 through Saturday, October 19: Martha’s Vineyard Striped Bass and Bluefish Derby
Now in its 74th year “The Derby” is a Vineyard fishing tradition that completely consumes local anglers, and those that visit the Island especially for it. Participants vie for big prizes including a car and a boat, and many of them don’t sleep until they catch a winning fish.
4. Saturday, September 21: 4th Annual Martha’s Vineyard Craft Beer Festival Beer lovers rejoice! Enjoy your pick of 150 beers from 50 breweries under a big tent at Waban Park in Oak Bluffs. Sample your favorites and discover new brews.
5. Through September: Sunset & Moonrise Kayak Tours
Join Felix Neck Wildlife Sanctuary for a paddle on Sengekontacket Pond and take in a breathtaking sunset or spectacular moonrise. Sit back, relax and appreciate the painted skies of Martha’s Vineyard.
6. Friday, September 27 & Saturday, September 28: Martha’s Vineyard Fashion Week
Returning after a five-year hiatus and hosted by Dressed MV, two shows will be held at the Vineyard Arts Project in Edgartown featuring looks from local designers including Conrado, Roy Bikini, American Rhino,The Green Room, Citrine x Trust, June, The Glasshouse and more. Tickets available in stores and online.
7. Saturdays through October 12: West Tisbury Farmers Market.
The open air West Tisbury Farmers Market was established in 1974 and has been operating ever since, making it the Island’s oldest market, and the go-to spot for the freshest food around. In the fall the market continues to pop up on Saturdays from 9-12pm at the Grange Hall in West Tisbury. The Market also returns in the winter and meets indoors at the Agricultural Hall in West Tisbury on Saturdays from October to December. Be sure to check the most current hours here.
8. Saturday & Sunday, October 12 & 13: The Art of Chocolate Festival
For eighteen years Featherstone Center for the Arts, the Island’s year round art haven in Oak Bluffs, has celebrated all things chocolate. This tasty festival features two days of all out chocolate consumption. Enjoy the heavenly experience of sampling every morsel of chocolate in any form your heart desires.
9. Sunday, October 13: Vineyard Artisans Columbus Day Festival
Vineyard Artisans resurrects its weekly summer festival especially for Columbus Day, offering the ultimate destination for shopping local on Martha’s Vineyard. Meet the artists themselves and browse their impressive products including textiles, fine furniture, pottery, leather goods, oil paintings, pastels, mixed media, sculpture, wampum jewelry, hand-knit items, clothing, photography, handmade books, and more.
10. Sunday, October 13: Popcorn Festival at Native Earth Teaching Farm
Pop in for free popcorn all day from 10am-3pm and enjoy fall fun at this small working educational farm in Chilmark.
11. Wednesday, October 23 through Sunday, October 27: Martha’s Vineyard Food & Wine Festival
This four day food and wine event brings together top culinary talents from the Island and beyond, along with world class winemakers, local farmers and discerning foodies for the ultimate taste of the Island experience. For the first time special guest and acclaimed chef Daniel Boulud will host an intimate five-course French dinner at Bettini Restaurant at the Harbor View Hotel.
12. October 19: Morning Glory Pumpkin Festival
The largest farm on Martha’s Vineyard hosts this lively free fall festival each year, complete with pumpkin games, hayrides, live music, and all things pumpkin.
13. Sundays through October: Oak Bluffs Open Market
Experience this super combination of Farmers Market, Artisan Fair, Vintage Flea Market and Body, Mind, Spirit Fair–all together at Washington Park in Oak Bluffs. The ever-changing variety of locally grown produce, specialty foods, flowers, indie designers, artisans and vintage dealers offers something for everyone…plus live music!
14. Wednesdays through October: Pizza Nights at Orange Peel Bakery
This charming up-Island bakery welcomes the community to stop by and enjoy pizza together every Wednesday night from 5-8pm through November. Show up with your favorite toppings, mingle with the locals and meet some new friends.
15. Saturdays through October: Honey Farm Bee Hive Tours
Experience the life of bees along with a beekeeper from Ginny Bee Honey Farms for a small group tour. Learn about the world of bees and how valuable they are to our food and our environment. You'll assist in finding the queen, measuring honey, identifying pollen, and monitoring bee life cycles.
16. Through mid-October: Take a Classic Aviators Biplane Ride
Take in the best view of Martha’s Vineyard from high in the sky. Enjoy breathtaking scenery and sights that can only be viewed from above while learning about the history of the Island.
17. The month of October Fall for the Arts
Each fall, Martha’s Vineyard, along with Cape Cod and Nantucket, dedicates the entire month of October to a celebration of the arts. Fall for the Arts strives to initiate and sustain conversations among artists, patrons, and the public.
18. Sunday, October 27: Happy Haunting
This event encompasses Edgartown’s annual Halloween festivities, and things can get spooky. Visit downtown Edgartown for some Halloween fun, while little ghosts and goblins trick-or-treat from business to business. Sponsored by the Edgartown Board of Trade.
19. Friday, November 15 - Friday, December 13: Featherstone Holiday Gift Show
Featherstone Center for the Arts is the place to go for unique, one of a kind holiday presents made right here on Martha’s Vineyard. It’s gifts galore for a whole month, including apparel and accessories, cards, calendars, jewelry, pottery, photography, paintings, ornaments, and more. All sales benefit local Vineyard artists and Featherstone, the Island’s only not-for-profit, year-round art center.
20. November 29: Felix Neck Wildlife Sanctuary Fall Festival
This celebration of fall is a Vineyard tradition. Held the day after Thanksgiving, it features hayrides, face painting, live music, food, wreath making, a weather station and crafts for kids, live animals, trail walk, and fun to be had by the whole family.
If you’ve ever researched Martha’s Vineyard you’ve likely come across photos of brightly colored gingerbread cottages. You may have even heard about the magical night of the year when the cottages glow with a profusion of colored lanterns. Perhaps you’ve even been lucky enough to attend this annual night of splendor. This year’s Grand Illumination (often referred to as Illumination Night) takes place on Wednesday, August 14 and marks the 150th year of this popular and important tradition - making it one of the most celebrated nights of the year. Here’s a look back at the history of the cottages and the annual event that brings thousands of visitors together to share in the splendor of their significance and charm.
A Movement is Born
Hundreds of Victorian cottages stand today on the grounds of the Martha’s Vineyard Camp Meeting Association (MVCMA), formerly known as Wesleyan Grove, which originally became a destination during the “camp meeting” movement of the 19th century. Methodists began gathering together on Martha’s Vineyard for summer retreats in pursuit of revival and renewal. In the beginning the camp meetings would last for several days and attendees would set up tents in a common area bringing with them provisions and supplies.
Eventually Wesleyan Grove in Oak Bluffs grew to become one of the largest and best-known camp meeting sites in the country. From nine tents in 1835 Wesleyan Grove grew to host 12,000 people and, in 1868, the number of tents reached 570. Initially the retreats were intended to be exclusively religious in purpose but eventually they became more social with attendees flocking to experience the chance to revitalize body and spirit.
People began to stay for longer periods of time and small wooden buildings began taking the place of tents. Between 1859 and 1864 the “Martha’s Vineyard” cottage emerged as a new architectural form that was celebrated and admired – as it still is today. There were about 40 cottages in 1864, 250 in 1869 and 500 by 1880. Today there are approximately 318 cottages remaining.
A Night of Lights
In 1869 the first Illumination Night was held. The event was called Governor’s Day in honor of the Governor of Massachusetts who had arrived to witness the highly anticipated spectacle. In efforts to impress the Governor, residents tried to outdo one another in the display of silk and paper lanterns and other forms of illumination with which they adorned their cottages.
Today Illumination Night or the Grand Illumination continues to be a time-honored tradition that brings together the community of the MVCMA and beyond. Thousands of paper and vintage silk lanterns are hung and admired each year. Attendees walk throughout the MVCMA appreciating the decoration, meeting with homeowners and mingling with other guests who have come to pay homage to this important tradition. Hailed as the most magical night on Martha’s Vineyard, attending Illumination Night is like taking a step back in time.
Celebrating Through the Centuries
The evening begins with a community sing and a concert by the Vineyard Haven Band at 7pm inside the Tabernacle, an open-air, octagonal structure in the heart of the MVCMA. Then, as darkness falls, the elaborate lanterns decorating the gingerbread cottages are illuminated in unison. This tradition will delight the whole family and leave both young and old with a feeling of unmatched enchantment.
Everyone is invited to walk the elaborate maze of homes inside the MVCMA and appreciate each cottage individually. Think back on what life was like back in 1869 and acknowledge the continued commitment that allows us to still make this event come to life 150 years later – and, hopefully for another 150 years to come. It’s a night steeped in history and community and a magical night not to be missed.
Illumination Night is free and open to the public but is supported with a free will offering. For more history on the event visit the MVCMA website.
Martha’s Vineyard is truly a music lover’s paradise. Our small Island is home to countless musicians, music venues and music-centric events that regularly showcase local and off-Island talent. Any night of the week in the summer season you’ll find live music to dance, sing, and sway along to, usually free of charge. Want to really experience those Island vibes? Check out some of these local go-tos for the ultimate song and dance on Martha’s Vineyard.
The Beat Goes On in OB
The Ritz MV, Oak Bluffs: The Island’s most iconic dive bar offers nightly live music and some of the best local talent around. This historic rock club has been entertaining bar-goers since 1944 and no visit to Martha’s Vineyard is complete without a stop in. You’ll find trivia and karaoke every Tuesday and some of the biggest Island names every other night of the week. There’s often an earlier show in the evening and a 10pm set too, all with no cover charge. And come hungry, there is nothing dive-y about their impressive and creative menu.
Nomans, Oak Bluffs: The latest addition to the Island music scene, Nomans just opened in June 2019 and has been entertaining visitors daily ever since. The family-friendly restaurant, which took over the former Lola’s space on Beach Road, offers live music throughout the day. You’ll find a casual and lively indoor/outdoor space with the expansive lawn as the star of the show. Grab a drink, grab a table, sit back and relax while you enjoy hours of free live music. It’s family- and dog-friendly and offers a full bar, counter service, a grab and go menu, and lawn games. Bring the family and spend the day!
Sand Bar & Grille, Oak Bluffs: Steps from the Oak Bluffs harbor, and conveniently located close Hyline, Island Queen and Steamship Authority docks in Oak Bluffs, this lively beach bar keeps the live tunes cranking on the weekends. Enjoy a delicious meal or relaxing cocktail with your toes in the sand, while the sun sets and the Vineyard nightlife ensues.
Park Corner Bistro, Oak Bluffs: This gastropub-style restaurant has only forty seats in the house and a farm-to-table approach to the menu. Visitors and locals alike flock to the bar for their craft cocktails and you’ll often find live music and DJs on weekends.
Portuguese-American Club, Oak Bluffs: Founded in 1930 as the Holy Ghost Association, this club, bar, and fundraising organization hosts social and community events, as well as live music concerts throughout the year.
The Cardboard Box, Oak Bluffs: The Cardboard Box is a restaurant built with “heart and soul” and diners are encouraged to eat, drink and revel. The revelry means diners can move and groove to local DJs most nights in this dimly lit, intimate and eccentric space.
Gettin’ Down in Edgartown
The Port Hunter, Edgartown: One of the most popular hot spots in Edgartown, this bar, restaurant and live music destination is always a fun time. You’ll want to get there early to try to score a seat at the bar. Enjoy something from the raw bar or from their main menu - the Buffalo Brussels are world famous. As the evening progresses, The Port Hunter turns into a music venue with regular shows starting at 10pm through October.
Seafood Shanty, Edgartown: This is the place to be when it comes to outdoor dining on Martha’s Vineyard, with DJs heating up the scene throughout the week. Overlooking Edgartown harbor the fish-focused restaurant boasts a casual dining room, an expansive deck, and a lot of dancing once the DJs arrive.
The Wharf, Edgartown: Located in downtown Edgartown, the family-friendly dining room features local seafood and classic pub favorites. Once night falls the lively back bar hosts regular events and live music.
Town Bar & Grill, Edgartown: This newly opened bar and restaurant boasts an expansive menu, weekend brunch, an impressive outdoor patio and regular live entertainment, including karaoke, acoustic sets, DJs and more.
Bad Martha’s, Edgartown: This Farmer’s Brewery and Tasting Room sits on the grounds of Donaroma’s Nursery and offers good brews, lawn games, and live jams. Check out their calendar on Facebook.
More Places to Boogie
In addition to live music venues on Martha’s Vineyard there are also several weekly musical events that happen throughout the summer. Don’t miss these free, family-friendly events!
Tuesdays: Unplugged Porch Concerts series hosted by mvyradio at the Harbor View Hotel; Sounds like Summer series on the Edgartown Library lawn sponsored by the Friends of Edgartown Public Library.
Thursdays: Music in the Square outside of the Eisenhauer Gallery in Edgartown.
Fridays: Sunset Concert Series in the Martha's Vineyard Camp Meeting Association (home of the iconic gingerbread cottages) on the Tabernacle lawn.
Sundays: The Vineyard Haven Band performs every Sunday at 8pm, location alternates between the bandshell in Owen Park, Vineyard Haven and the Ocean Park gazebo in Oak Bluffs.
For a complete list of daily and weekly events on Martha’s Vineyard this summer click here.
Visit Martha's Vineyard
Loving Martha's Vineyard is the easiest thing in the world to do.