A Bucket List of Things to Do on your 2025 Martha's Vineyard Trip - Start Planning Now! 

 

Planning a trip to Martha's Vineyard in 2025? This charming island offers a plethora of activities that cater to every interest. Whether you’re an art lover, history buff, outdoor enthusiast, or foodie, there’s something here for you. Here’s a comprehensive bucket list to ensure you make the most of your visit, complete with examples for each activity.

 

1. First Friday Artist Market Kick off your month by visiting the First Friday Artist Market in Vineyard Haven. Browse unique pieces like hand-painted seascapes, intricate jewelry, and ceramics crafted by local artists.

 

2. Aquinnah Cliffs The stunning Aquinnah Cliffs are a must-see. These colorful clay cliffs, rising dramatically above the Atlantic, are perfect for a scenic hike. Don’t forget to stop by the nearby Gay Head Lighthouse for a panoramic view.

3. Gingerbread Cottages Stroll through the enchanting Gingerbread Cottages in Oak Bluffs. These whimsical, brightly painted houses, each with its own story, are perfect for a picturesque afternoon walk and photography session.

 

4. African American Heritage Trail Explore the rich history of African Americans on the island by following the African American Heritage Trail. Visit sites like the Shearer Cottage, a historic inn, and the home of Dorothy West, a noted Harlem Renaissance writer.

 

5. Flying Horses Carousel Take a ride on the Flying Horses Carousel, the nation’s oldest operating platform carousel. Grab a brass ring to win a free ride while enjoying the nostalgic charm of this Oak Bluffs landmark.

6. All FIVE Lighthouses No trip to Martha’s Vineyard is complete without visiting its five iconic lighthouses: Edgartown, East Chop, Gay Head, West Chop, and Cape Poge. Climb to the top of Edgartown Lighthouse for stunning harbor views or explore the remote beauty of Cape Poge by bike.

7. Menemsha Sunset Head to Menemsha to witness one of the most breathtaking sunsets on the island. Bring a picnic from the Menemsha Fish Market and enjoy the view as the sun dips below the horizon.

 

8. Fall for the Arts Autumn is a vibrant time on Martha’s Vineyard, thanks to the Fall for the Arts festival. Enjoy events like live music at the Grange Hall in West Tisbury or art exhibitions at Featherstone Center for the Arts.

 

9. Martha’s Vineyard Museum Dive into the island’s history at the Martha’s Vineyard Museum. Check out the Fresnel lens from the Gay Head Lighthouse or the exhibit on the island’s whaling history.

 

10. Island Alpaca Farm Visit the Island Alpaca Farm in Vineyard Haven to meet these adorable creatures up close. Join a guided tour to learn about alpaca farming and even try your hand at feeding them.

 

11. MV Striped Bass & Bluefish Derby Anglers will not want to miss the MV Striped Bass & Bluefish Derby. Participate in this beloved fishing competition and aim to catch the biggest fish for a chance to win great prizes.

 

12. Full Moon Paddle Boarding or Kayaking Experience the island’s waterways in a magical way with full moon paddle boarding or kayaking. Join Island Spirit Kayak for a guided moonlit tour of Sengekontacket Pond.

 

13. The Agricultural Fair Celebrate the island’s agricultural heritage at the Agricultural Fair in West Tisbury. Enjoy livestock shows, watch the antique tractor pull, and indulge in classic fair food like fried dough and homemade pies.

 

14. South Beach Stargazing On a clear night, head to South Beach for some incredible stargazing. Bring a telescope or simply lay back on a blanket to watch the Milky Way and shooting stars.

 

15. Cape Poge & Chappaquiddick Explore the natural beauty of Cape Poge Wildlife Refuge and Chappaquiddick Island. Take an over-sand vehicle tour with The Trustees to see the barrier beach, salt marshes, and diverse wildlife.

 

16. West Tisbury Farmers Market Support local farmers and artisans at the West Tisbury Farmers Market. Pick up fresh produce like heirloom tomatoes, homemade jams, and artisanal breads.

 

17. Oak Bluffs Fireworks Don’t miss the spectacular Oak Bluffs Fireworks, a dazzling display that lights up the summer sky and is a highlight of the season. Arrive early to snag a good spot near Ocean Park.

18. Back Door Donuts Indulge in a late-night snack at Back Door Donuts in Oak Bluffs. Try their famous apple fritters or Boston cream donuts, freshly made and delicious.

 

19. Martha’s Vineyard Artisans Festivals Browse through the Martha’s Vineyard Artisans Festivals, where local artists and craftspeople showcase their talents. Find unique souvenirs like hand-woven baskets and locally made soaps.

 

20. Bike Trail Rides Explore the island’s scenic beauty on two wheels. Ride the State Forest bike path or take the ferry to Chappaquiddick and bike through Mytoi Japanese Garden and Cape Poge.

 

21. Edgartown Captains’ Houses Take a walking tour of Edgartown to admire the historic captains’ houses. These elegant homes, like the Vincent House Museum, reflect the island’s rich maritime history.

 

22. The Martha’s Vineyard Playhouse Catch a performance at The Martha’s Vineyard Playhouse, which hosts a variety of theatrical productions throughout the year. Don’t miss their summer Shakespeare series.

 

23. Go for a Hike Discover the island’s natural landscapes by hiking one of its many trails. Explore Menemsha Hills for stunning views of Vineyard Sound or hike the trails at Long Point Wildlife Refuge.

 

24. Polly Hill Arboretum Wander through the Polly Hill Arboretum in West Tisbury. Enjoy the serenity of the gardens, featuring rare trees and plants, and join a guided tour to learn more about the collections.

 

25. Ice Cream Treat yourself to some delicious ice cream from one of the island’s many ice cream shops. Try Mad Martha’s for a scoop of their famous Vineyard Crunch or a cone from Scoops on Circuit Avenue.

 

26. Inkwell Beach Sunrise Start your day with a sunrise at Inkwell Beach in Oak Bluffs. The serene morning light and gentle waves create a peaceful atmosphere perfect for a morning meditation or jog.

 

27. Sightseeing Tours Join a sightseeing tour to learn more about the island’s history, landmarks, and hidden gems. Opt for a narrated bus tour with Island Transport for an informative overview.

 

28. Film Festivals Film enthusiasts will enjoy the island’s various film festivals, which showcase a diverse array of films from independent and international filmmakers. Attend the Martha’s Vineyard Film Festival for thought-provoking documentaries and Q&A sessions with filmmakers.

 

29. Lady Fest Concert Experience the Lady Fest Concert, a celebration of female musicians and artists. Enjoy live performances from talented women in the arts and immerse yourself in the empowering atmosphere.

 

30. Felix Neck Wildlife Sanctuary Visit the Felix Neck Wildlife Sanctuary to explore its trails and observe local wildlife. Participate in a guided bird-watching tour or attend a nature program for kids.

 

31. Visit all SIX Island Libraries Make it a goal to visit all six of the island’s libraries. Each one has its own unique charm and offers a cozy spot to read and relax. Don’t miss the West Tisbury Library’s beautiful reading garden.

 

32. Golf, Mini-Golf & Disc Golf Whether you prefer traditional golf, mini-golf, or disc golf, the island has plenty of options to enjoy a game with friends and family. Try the Farm Neck Golf Club or the mini-golf course at Island Cove Adventures.

 

33. Bowling Head to the Barn, Bowl & Bistro in Oak Bluffs for a fun and casual activity. Enjoy a few rounds of bowling, then relax with some food and drinks in the bistro.

 

34. Fishing Charter Book a fishing charter to experience the thrill of deep-sea fishing. Join a trip with Skipper Charters and try to reel in striped bass, bluefish, or even a shark.

 

35. Carnegie Heritage Center Learn about the island’s African American heritage at the Carnegie Heritage Center in Edgartown. Explore exhibits and collections that provide fascinating insights into the island’s history.

 

36. Alley’s General Store Step back in time with a visit to Alley’s General Store in West Tisbury. Browse the eclectic mix of goods, from local produce to quirky gifts, and enjoy the nostalgic atmosphere.

37. Oak Bluffs Open Market Explore the Oak Bluffs Open Market, where you can find fresh produce, handmade crafts, and unique gifts. Enjoy live music and delicious food from local vendors.

 

38. Visit Local Cheese & Farm Stands Taste the island’s local flavors by visiting cheese and farm stands. Try artisanal cheeses from Grey Barn and fresh vegetables from Morning Glory Farm.

 

39. Morning Glory Strawberry Festival Celebrate the strawberry season at the Morning Glory Strawberry Festival. Enjoy strawberry shortcake, live music, and family-friendly activities on the farm.

 

40. Living Local Harvest Festival Join the community at the Living Local Harvest Festival, which promotes sustainable living and local agriculture. Participate in workshops, enjoy local food, and celebrate the island’s farming heritage.

 

41. Oak Bluffs Arts District Explore the Oak Bluffs Arts District, home to galleries and studios showcasing local artists. Visit the Arts District Stroll to meet the artists and view their latest works.

 

42. Grace Church Lobster Roll Treat yourself to a famous lobster roll from Grace Church in Vineyard Haven. Enjoy this local favorite, freshly made and served every Friday in the summer.

 

43. Chicken Alley Thrift Store Browse for treasures at the Chicken Alley Thrift Store in Vineyard Haven. Find unique items, vintage clothing, and support a great cause with your purchases.

 

44. Juneteenth Jubilee Celebrate Juneteenth with the island community. Enjoy cultural events, performances, and activities that honor African American history and freedom, such as the Jubilee parade and festival.

 

45. A Very Vineyard Holiday Experience the magic of the holidays on Martha’s Vineyard with festive events and decorations that create a cozy and cheerful atmosphere. Enjoy holiday lights tours and special seasonal performances.

 

46. Run a Road Race Challenge yourself by participating in one of the island’s road races. Join the Martha’s Vineyard Marathon or the Chilmark Road Race for a scenic run and community spirit.

 

47. Christmas in Edgartown Enjoy the holiday season with Christmas in Edgartown. Experience the festive atmosphere with a parade, holiday shopping, and the annual lighting of the lighthouse.

 

48. Self-Guided Deaf Heritage Tours Take a self-guided tour to learn about the island’s Deaf heritage. Use the tour map to visit significant sites and read about the island’s unique Deaf history.

 

49. Bi-Plane Rides For a unique perspective, take a bi-plane ride over Martha’s Vineyard. Enjoy breathtaking aerial views of the island’s coastline, lighthouses, and landscapes with Classic Aviators.

 

50. Chilmark Flea Market Find unique treasures at the Chilmark Flea Market. Browse through antiques, handmade crafts, and local art while enjoying the outdoor market atmosphere.

 

51. Outdoor A Capella Concert Enjoy the beautiful harmonies of an outdoor a capella concert. Attend performances by groups like Vineyard Sound, who sing in various locations around the island during the summer.

 

52. Featherstone Center for the Arts Visit the Featherstone Center for the Arts in Oak Bluffs. Participate in art workshops, view exhibitions, and attend cultural events in this creative community space.

 

53. MV Food & Wine Festival Savor the flavors of the island at the MV Food & Wine Festival. Enjoy tastings, chef demonstrations, and wine pairings from local and guest chefs.

 

54. The Yard Experience contemporary dance and performance art at The Yard in Chilmark. Attend a summer performance or take a dance class to immerse yourself in the arts.

 

55. Field Gallery Sculpture Garden Wander through the Field Gallery Sculpture Garden in West Tisbury. Admire whimsical sculptures set amidst beautiful gardens and explore the gallery’s rotating exhibits.

 

57. Tivoli Day Street Festival Join the fun at Tivoli Day, a street festival in Oak Bluffs. Enjoy live music, food vendors, and family-friendly activities as Circuit Avenue comes alive with festivities.

 

58. Menemsha-Aquinnah Bike Ferry Take the Menemsha-Aquinnah Bike Ferry for a unique and scenic way to travel between these two iconic island locations. Enjoy the ride and the opportunity to explore both areas by bike.

 

59. Long Point Wildlife Refuge Explore the diverse landscapes of Long Point Wildlife Refuge. Hike through coastal dunes, woodlands, and freshwater ponds, or relax on the pristine beach.

 

60. Edgartown Harbor Spend time at Edgartown Harbor, where you can watch boats come and go, take a sailing lesson, or simply enjoy the views from a waterfront cafe.

61. Oyster Farm Tours Learn about aquaculture on an oyster farm tour. Visit farms like Cottage City Oysters to see how oysters are grown and harvested, and taste fresh oysters straight from the sea.

 

62. Grand Illumination Night Experience the magic of Grand Illumination Night in Oak Bluffs. Stroll through the Campground as the Gingerbread Cottages are illuminated with colorful lanterns.

 

63. Shakespeare at the Amphitheater Enjoy a Shakespearean play performed at the Tisbury Amphitheater. The outdoor setting adds a special touch to classic works like "A Midsummer Night’s Dream" or "Romeo and Juliet."

 

64. Oak Bluffs Harbor Fest Join the festivities at Oak Bluffs Harbor Fest. Enjoy live music, local food vendors, and family-friendly activities along the picturesque harbor.

 

65. Orange Peel Bakery’s Pizza Night Experience community dining at Orange Peel Bakery’s Pizza Night in Aquinnah. Bring your own toppings and create your pizza, then bake it in the outdoor wood-fired oven.

 

66. The Chilmark Store Visit The Chilmark Store for a taste of local flavor. Grab a slice of pizza, a fresh sandwich, or a cup of coffee and relax on the porch with locals and visitors alike.

 

67. Jaws Filming Locations Tour the iconic filming locations of the classic movie "Jaws." Visit places like Menemsha Harbor and South Beach, and imagine the thrill of the famous shark scenes.

 

68. Mytoi Japanese Style Garden Find tranquility at the Mytoi Japanese Style Garden on Chappaquiddick. Wander through the serene gardens, featuring koi ponds, footbridges, and beautiful plantings.

 

69. Taste of the Vineyard Indulge in the culinary delights of the island at the Taste of the Vineyard. Sample food and wine from top island chefs and vineyards while enjoying live music and dancing.

 

With so many incredible activities to choose from, your visit to Martha’s Vineyard in 2025 will be unforgettable. Make sure to check off as many items as you can from this bucket list to fully experience the charm and beauty of the island.