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Things to Do in Maine in September

Maine is a popular vacation destination during the late spring and summer months and is known for its warm, inviting weather and gorgeous beaches. But what if your trip to the Pine Tree State is scheduled for after summer has ended?

Don’t worry — there are still plenty of ways to enjoy this beautiful state and create incredible memories with your family during the autumn months. In fact, Maine in September has certain special qualities to offer locals and visitors alike that you simply won’t see throughout the rest of the year.

Things to Do in Maine in September for Family Fun

  1. Visit Family Harvest Days
  2. Spend the Day at the Pemaquid Oyster Festival
  3. Go Whale Watching
  4. Hop on the Pumpkin Trail
  5. Explore the Boothbay Harbor Fest
  6. Enjoy the Fall Colors
  7. Take a Spooky History Tour

A beach day may seem less enticing as the weather in Maine starts to cool off, but there are still many ways to enjoy this plentiful state in September. Even if you may not be lying out in a bathing suit, there are lots of outdoor activities to do with your family and friends.

Visit Family Harvest Days

A trip to Family Harvest Days is the perfect activity for a family visiting New England in the fall. This popular festival is held each September in Maine and features lots of fun and family-friendly activities, including pumpkin decorating, hayrides, petting zoos, and much more.

Additionally, there’s so much to explore around the Boothbay Railway Village, which hosts Family Harvest Days. You can learn about the history of the railroad in New England, visit some of the quaint local shops, and experience firsthand what life was like in a small town in Maine over 100 years ago!

Spend the Day at the Pemaquid Oyster Festival

It’s no secret that one of the best things to do in Maine in September (or any time of year) is to enjoy some fresh-caught oysters. If you’re particularly fond of oysters and have a trip to Maine planned for September, you’re in luck!

The Pemaquid Oyster Festival takes place each September in downtown Damariscotta right along the river. Aside from plenty of delicious oyster dishes to try, attendees of this event can also enjoy live music, scenic boat tours, and stunning riverside views.

Go Whale Watching

Whale watching is a classic activity along the east coast that can be enjoyed during any time of year, but it is particularly popular in autumn as the weather starts to cool.

One of the most sought-after things to do in Maine in September is to book a tour with Cap’n Fish’s Cruises. This company’s premier whale-watching excursions set sail out of Boothbay Harbor.

Multiple excursions take place each day with Cap’n Fish’s Cruises, including whale-watching tours along popular feeding grounds, lighthouse visits, Kennebec River cruises, and sunset cocktail cruises. Learn more: A Quick Guide to Whale Watching Near York, Maine.

Hop on the Pumpkin Trail

If you’re looking to truly enjoy the Maine coastline firsthand with some adventuring, one of the best things to do in Maine in September is to plan a trek on the Pumpkin Trail.

This 50-mile trail covers a huge majority of the Maine coast and includes several hiking trails, pumpkin smashing, train rides, cruises, and more. It’s easy to see why the Pumpkin Trail is one of the most highly anticipated parts of the yearly Damariscotta Pumpkin Festival.

Explore the Boothbay Harbor Fest

The fishing industry is a huge part of the local culture throughout many Maine cities and towns, and the Boothbay Harbor Fest is the best place to showcase this.

This ten-day event dives deep into the nautical history (and present) of the entire state of Maine and connects visitors with representatives from some of Maine’s most beloved cultural, arts, community, and wellness organizations.

Other activities to enjoy during this festival include the Harbor Fest 5K, A Taste of Local Flavor passports to help explore the local grub, and live music to entertain you as you peruse the event.

Enjoy the Fall Colors

It’s great to have some specific activities on the docket for your September trip to Maine, but it’s also important to schedule some time to simply enjoy the scenery.

September is the time of year when the colors start to change in New England, and a simple drive down the coast could bring you some incredible sights. Baxter State Park is a particular favorite among locals for changing leaves and cool fall weather. Check out our list of scenic drives in Maine.

Take a Spooky History Tour

Many of Maine’s towns have been around for hundreds of years, leading to plenty of local lore that includes some spooky ghost stories and haunted buildings. If your family is into all things paranormal, there are plenty of spots throughout the state to take a spooky history tour and learn more about the local haunts.

Red Cloak Haunted History Tours is a big name in Maine for just this kind of family fun. It hosts 90-minute walking tours throughout autumn in multiple Maine locations.


Stage Neck Inn is an iconic destination where families and friends share delightful experiences that evolve into lifetime memories. Offering spacious accommodations with modern amenities and classic décor, breathtaking ocean and harbor views and the ocean’s relaxing sounds make for the perfect stay at our oceanfront resort in York Harbor, ME. Book your stay online now.