Martha’s Vineyard in October: 14 Reasons Fall is a Great Time to Visit

Is October a good time to visit Martha’s Vineyard? While most people think of Martha’s Vineyard as a summer destination, you might be surprised to learn how much is still going on this month on the island.

October is one of the most affordable and peaceful times to visit. There’s no traffic, fall festivals are in full swing and plenty of restaurants and stores are still open. 

I am always surprised at how nice the weather can be this month. Cool in the shade but blissfully warm in the direct sun, you can still enjoy a last barefoot walk on a beautiful beach or one more lobster roll picnic in Menemsha!

Here’s what you need to know about things to do in Martha’s Vineyard in October, plus what to pack, how to get there, where to stay and what’s open at this time of year.

Off-Season Things to do on Martha’s Vineyard in October

1. Join the Martha’s Vineyard Striped Bass and Bluefish Derby

When: Through October 18th, 2025 | Where: Island-wide

This legendary fishing tournament has been running since 1946 and remains one of the island’s most beloved traditions. Even if you’re not a fisherman, spectators are always welcome to cheer on the participants and experience the excitement at the daily weigh-ins.

My favorite time to go is on the last day. The tension is palpable as the leaders hope and pray they won’t be knocked off the top spot at the last-minute! Visit Derby headquarters at Dock. st in Edgartown between 8am and 10am or in the evenings from 7-9pm. 

2. Have fun at the Harvest Festivals 

When: October 11th, 18th & 25th 2025 | Where: West Tisbury, Edgartown

Harvest festivals embody everything wonderful about New England in autumn. At Vineyard Gardens on Oct 11th, stroll through the nursery bursting with fall colors, enjoy seasonal baked goods, chili, hot dogs and fresh apple cider. There’ll be hands-on crafts and games and all ages are welcome at this free event 

I really enjoy the Martha’s Vineyard Agricultural Society Harvest festival (Oct. 25th). It’s a relaxed, family-friendly event featuring tons of entertaining activities like cow chip bingo, pumpkin carving, a hay bale maze, corn-husking contest, wagon rides, and a pie-eating contest.

Local bands and food trucks provide live music and refreshments. This is one of my top recommendations for your trip to Martha’s Vineyard in the fall. If you love the summer Ag Fair, you’ll love this festival too!

Morning Glory Farm’s annual pumpkin festival takes place on the 18th, (10:30-2:30) and is always a great day of fun. There’ll be hay rides, a maize maze, pumpkin launching from a trebuchet, a haunted greenhouse, kid’s games, pumpkin carving, live music and more!

3. Tee Off in The Martha’s Vineyard Golf Series

When: October 24th-26th, 2025 | Where: Edgartown, Vineyard Haven

Golf enthusiasts won’t want to miss this exceptional three-day tournament series presented by Cape Cod Golf Guys. You can participate in one, two, or all three unique tournaments on incredible island golf courses.

The Opener (24th) offers a rare opportunity to play the exclusive Vineyard Golf Club. Tee times are between 11:00 AM-1:00 PM and entry is $350. This fee includes 18 holes, on-course snacks, player gifts, and prizes for top individual and foursome scores.

Bird Fest IV (25th) takes place at the Royal & Ancient Chappaquiddick Links. You’ll have to hop on the Chappy ferry to get to this legendary course! Play as many nine-hole rounds as you want between 9 AM-2 PM, recording only your best score on each hole.

The day includes multiple trips around the course, pizza lunch, and special prizes for birdies and eagles. Top tip: While you’re on Chappaquiddick, visit Mytoi Japanese Garden to see the fall foliage.

Mink-Mosa (26th) concludes the series at Mink Meadows with an 8:00 AM shotgun start. This creative format features two loops of the nine-hole course with different pin positions, plus breakfast refreshments and prizes for the lowest scores.

4. Take a Kayak Tour

When: October 2025 | Where: Edgartown

It’s not too late to take a kayak tour! Yes, October may be a little cooler than the summer months but wear an extra layer and you can still get out on the water and see the island from a different perspective

If you have some experience, rent kayaks from Island Spirit and head out on Sengekontacket Pond, or book a tour with a guide. This is my favorite way to go because the guides always point out new and interesting things I haven’t seen before.

You can also take sunset tours at Felix Neck with a Mass Audubon naturalist guide on October 18th (ages 14+)

5. Support the Bass in the Grass Fundraiser

When: Through October 19th 2025 | Where: Carnegie Museum, Edgartown

Derby season is not just for fishing! Bass in the Grass is a fundraiser for local artists, the EBT, and the Derby Scholarship Fund. Artists create fish-inspired sculptures that go up for auction at the end of the Derby.

Each piece is completely unique, made from carved and hand-painted wood, metal, or other materials like beach-wood or rope found on island beaches. 

The Bass are on display at The Carnegie Museum in Edgartown and you can place your bids online until October 19th

6. Meet the Horses at Ponies and Pumpkins

When: October 25th, 2025 | Where: Misty Meadows Equestrian Center, West Tisbury

Ponies and Pumpkins features kids’ games, pumpkin decorating, face painting, a bake sale, and fresh cider, plus the special opportunity to interact with the gentle Misty Meadow horses. This community event runs from 10am to 12pm and donations are appreciated.

Bonus Tip: Can’t make it on the 25th? Visit on October 1st at 11am to meet the horses and enjoy pony story time and songs with Hannah from the West Tisbury Library.

7. Take a Day Trip for First Friday in Vineyard Haven

When: October 3rd, 2025 | Where: Vineyard Haven Harbor 

This free celebration transforms Vineyard Haven into an outdoor art and culture festival. There’s a daytime art and crafts market on Beach Street and evening live music at Owen Park. 

If you’re thinking of a fall day trip to Martha’s Vineyard, this is a good day to do it. You can walk right off the ferry and into the festivities, making it perfect for a day trip from Cape Cod.

Galleries and stores stay open late, seafood and other local specialties are available from the food vendors and live music continues well into the evening.

8. Run on Scenic Island Roads

When: October 5th, 11th & 18th, 2025 | Where: Aquinnah and Oak Bluffs

The weather in October is ideal for running and being outdoors and these three race routes showcase some of the island’s best scenery. The Gay Head Run for the Light 10K on October 5th takes you from the iconic Aquinnah cliffs down State Road and back to the lighthouse via Moshup Trail.

The Oak Bluffs School 5K on October 11th is JAWS-themed this year for the 50th anniversary,  complete with limited-edition race t-shirts. The route winds through the streets of Oak Bluffs and along East Chop, offering runners stunning ocean views and glimpses of the area’s beautiful homes. 

On October 18th, The Martha’s Vineyard Brunch Run is a three-in-one, with a one miler for under 14’s, a 5k run/walk and a 10k run. The route takes you along the scenic Atlantic Drive, past South Beach, Katama. Participants will take home a t-shirt and custom commemorative brunch glass.

9. Learn Fly Casting at Edgartown Lighthouse Beach

When: Every Wednesday, 3-4pm | Where: Edgartown Lighthouse Beach (North Water Street)

If the excitement of the Derby has inspired you to learn how to fish, you can get started at Kismet Outfitters group casting lessons on Wednesdays in October. Led by Captain Abbie Schuster, everyone is welcome – from complete beginners to experienced anglers looking to improve their technique.

All equipment is provided and you get to hang out at the beautiful Lighthouse Beach. What a perfect way to try something new while visiting Martha’s Vineyard in October.

10. Browse the Vineyard Artisans Fall Festival

When: October 11th-12th, 2025 | Where: Union Chapel, Oak Bluffs

This two-day festival showcases over 70 local artisans selling everything from handwoven items to pottery, paintings, and jewelry. Many artists offer live demonstrations, giving you the chance to see their craft in action.

You may not be thinking about holiday shopping just yet, but fall is your chance to get ahead of the holiday rush and this festival is a great time to pick up some unique pieces.

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11. Rock Out at Ladyfest MV

When: October 11th, 2025 | Where: Waban Alley Park, Oak Bluffs

This annual music festival features an impressive lineup including Esperanza Spalding and other talented performers. The event raises funds for CONNECT To End Violence while providing a family-friendly day of music and community.

Beyond the music, you’ll find local food vendors, artists selling jewelry, clothing, and artwork. Tickets are $50 and kids under 12 go free.

14. Celebrate Halloween on Martha’s Vineyard

When: October 25th-31st, 2025 | Where: Island-Wide

October wouldn’t be complete without mentioning the island’s fantastic Halloween celebrations. If you have little kids, it’s worth planning an October trip around this time.

Halloween in Oak Bluffs on October 25th 2025 is one of the biggest events of the weekend. Between 1 and 4pm, there’ll be trick-or-treating through downtown businesses on Main Street and a party at the Flying Horses.

The Halloween costume parade starts at Washington Park at 2.15 and makes its way to the Flying Horses for the costume competition at 2.30.

You can make your way back to Washington Park afterwards for the trunk or treat fundraiser with pumpkin decorating, horse-drawn carriage rides and face-painting from 3-5

Edgartown’s Happy Haunting celebration takes place the next day, October 26th with trick-or-treating from business to business in town.

Circuit Arts presents Spirits and Spirits (Oct. 28th – 31st 2025) at the Grange Hall in West Tisbury is a Halloween activity for the grown-ups. The evening begins with seasonal drinks like mulled wine and cider, plus autumn treats, followed by spine-tingling storytelling performances by local artists.

Tickets for Spirits and Spirits go on sale October 1st.

If the weather turns chilly, you can still celebrate the season at The Strand Theatre in Oak Bluffs as they typically show family-friendly spooky movies at this time of year.

Dress your pup for the costume competition at Howl-a-ween Bark and Boo Bash on October 31st at the Chamber of Commerce office.

There’ll be prizes for creative, cute and best overall costumes as well as photo opportunities and trick-or-treating stations with pet AND people-friendly treats. A portion of proceeds goes to the Martha’s Vineyard Animal Shelter.

The West Tisbury Library Halloween Party is on October 31st. Wear a costume, take a hayride, play some games and enjoy spooky treats to eat. There will be trick-or-treating at the nearby Field Gallery and Council on Aging.

Also on the 31st, from 4.30 – 6pm, Halloween on the Hill returns to the MV Museum, with trick-or-treating, seasonal crafts, games, candy and popcorn. Costumes are encouraged and there’s a sensory space for those needing a quiet escape

Boo in the Barnyard on October 25th at The FARM Institute is a family-friendly Halloween event, where you can treat the farm animals to snacks while picking up a few treats for yourself. Costumes are encouraged!

My top tips for a getaway to Martha’s Vineyard in October

Embrace the shoulder season ferries – October is your last chance to enjoy seasonal ferries before they close for the winter. The Island Queen from Falmouth, Hy-line from Hyannis and the Seastreak from New Bedford all begin winding down in October.

If any of these ferries are more convenient for you than travelling from Woods Hole, plan your trip for early October before your options become much more limited.

Bring or rent a car to get around the island – October is one of the best times to have a vehicle on Martha’s Vineyard. Reservations are easier to get, traffic is essentially nonexistent, and there’s no problem finding parking.

Having a car gives you the freedom to visit remote locations like the fishing village of Menemsha, plus the time to explore the whole island at your own pace.

Plan around Columbus Day weekend – Columbus Day weekend marks a turning point on the island. If you’re looking for a more lively atmosphere with the most restaurants and shops open, visit before Columbus Day.

However, if you prefer more peace and quiet, plan to come after the holiday. Many venues close or reduce their hours after that weekend, but accommodation rates are lower from then on. This is a wonderful time for shopping as stores have sales to reduce inventory before closing.

October is the perfect time for a day trip to Martha’s Vineyard – The combo of comfortable weather, smaller crowds, and multiple ferry options makes the fall season ideal for a day trip.

Early in October there are lots of fall activities taking place, plus plenty of dining options as most restaurants are still open. It’s so enjoyable to get to experience the island’s amazing seafood and fresh produce without the long table waits you get during the summer.

How to get to Martha’s Vineyard in October

In October, ferry services start to shift to their off-season schedules, but you still have options for getting to this beautiful island!

Ferry to Martha’s Vineyard in October

The Steamship Authority ferry from Woods Hole to Vineyard Haven operates year-round and is always the most dependable option. It’s a 45-minute journey, boats run frequently throughout the day and it’s the ferry I always take for October visits.

Make a reservation if you want to bring your car, but foot passengers don’t need to book in advance. These seasonal ferries travel to Martha’s Vineyard in October 2025:

• Seastreak from New Bedford (until Oct 13th)
• Island Queen from Falmouth (until Oct 13th)
• Hy-Line from Nantucket (until Oct 19th)
• Hy-Line from Hyannis (until Oct 26th)

Fly to Martha’s Vineyard in October

Jet Blue and Cape Air operate direct flights from Boston Logan and New York JFK throughout October. Jet Blue also flies direct from Washington DC on very limited dates up til October 13th. 

Martha’s Vineyard airport is located right in the middle of the island, so it’s easy to grab a taxi, rental car or the bus upon arrival to begin your island adventure.

Where to stay in Martha’s Vineyard in October

Many hotels and inns remain open through October, and you’ll find some of the year’s best rates during this period, especially post-Columbus Day.

October is also a good time to try a vacation rental property, which are often available at significant discounts compared to their peak summer rates. 

These hotels are open in October:

Edgartown

• Faraway Martha’s Vineyard
• Charlotte Inn
• The Edgar Hotel
• The Franklin Hotel
• Harbor View Hotel
• Edgartown Commons
• Hob Knob
• The Richard

Oak Bluffs

• Summercamp
• The Island Inn
• The Morgan Hotel
• The Oak Bluffs Inn

Vineyard Haven

• The Mansion House
• Vineyard Harbor Motel
  

Restaurants Still Open on Martha’s Vineyard in October

At this time of year, almost all the top restaurants and bars on the island are still open. Vineyard Haven is my favorite town for excellent dining options and the restaurants there often stay open longer in the season to serve the year-round population.  Here are some of my favorites from around the island: 

Edgartown

• Dock Street Coffee Shop
• Edgartown Diner
• The Wharf
• Atria
• Bad Martha’s
• Alchemy
• Bettini
• Espresso Love
• Town Bar and Grill

Oak Bluffs

• Barn Bowl and Bistro
• Farm Neck Cafe
• Lookout Tavern
• Offshore Ale Co.
• Mo’s Lunch
• Tigerhawk Sandwich Co.
• Martha’s Vineyard Chowder Company

Vineyard Haven

• Black Dog Bakery
• Black Dog Tavern
• Waterside Market
• 9 Craft Kitchen
• S&S Kitchenette
• La Strada
• Catboat Coffee Co.

Up-Island

• Menemsha Fish Market
• Orange Peel Bakery
• 7a Foods

Martha’s Vineyard October: Weather

The weather in October is what makes Martha’s Vineyard one of the best places to visit in the fall. When I was there at the end of October in 2024, it was 74°F and sunny all weekend!

Unfortunately, that’s not typical and there is normally a sharp fall in temperatures from the beginning of the month to the end. Average highs hover around 60°F, with lows dipping to around 54°F. 

This kind of weather is ideal for outdoor activities like hiking, biking and running. Kayak tours at Sengekontacket Pond (opposite Joseph Sylvia State Beach) are still available, although water temps are chilly by October.

What to Wear in Martha’s Vineyard in October

Layers are your best friend for a fall visit to Martha’s Vineyard. I typically wear pants or jeans at this time of year. Even if the sun is shining, the air still has a crispness to it and if there’s a breeze, it’s generally not a warm one.

On top, I’ll opt for a t-shirt or tank top and a light sweater, button-down shirt, fleece or blazer.  If you plan to walk on the beach, it’s often warm enough to go barefoot but you’ll probably still need jeans and a chunky sweater plus a windproof outer layer.

You’re unlikely to need swimwear (unless your hotel has a heated pool) and it’s not cold enough yet for hats, gloves or a scarf.

Don’t forget waterproof gear as there can be occasional showers, but the rain is unlikely to be heavy enough that you’ll need rubber boots. Comfortable walking shoes are essential if you’re going to be exploring on foot. 

Cozy coastal chic is the vibe rather than formal wear and don’t forget your sunglasses!

Final Thoughts: Is Martha’s Vineyard worth visiting in October?

If you usually visit Martha’s Vineyard in the summer, I highly recommend taking a trip in October. You’ll get to see the island in a whole new light.

The practical advantages are real too. No traffic jams getting to Menemsha for sunset. Easy parking in Edgartown. Multiple ferry options for most of the month. Hotel rates that won’t break the bank.

Sure, you might need a sweater for your beach walks, and a handful of shops and restaurants may be closed, but that’s a small trade-off for experiencing the island when it feels more like the year-round community it actually is.

Have questions about planning your October trip? Join the Martha’s Vineyard Travel Tips Facebook Group where you can get personalized recommendations and connect with other visitors and locals who know the island inside and out.