Kennebunkport Maine Bucket List: 20+ Things To Do in The Coastal Town

In the Southern part of Maine you will find the charming coastal town of Kennebunkport. It is the place most commonly known as being the summer home of former president George H. W. Bush. But, there is so much more to Kennebunkport besides ogling Walker’s Point, the location of the Bush compound. It is also a city where you can take your beloved pooch on a foodie tour, kayak on the river and indulge in fresh lobster at every meal.

Kennebunkport is a remarkable New England town that offers a unique travel opportunity to all tourists for all seasons. Whether traveling solo or with your family, here are the best things that you can do to enjoy Kennebunkport.

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The Best Things To Do in Kennebunkport Maine

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1. Catch a live show at Vinegar Hill

Enjoy a high-caliber live performance at Vinegar Hill Music Theatre and indulge in a unique entertainment experience that this beautiful town has to offer. This theater is nothing like your typical performance hall—it used to be a barn that was built in the late 1800s and has served its original purpose for over a century. It was in 1997 when the barn was given a new life and was transformed into a theater. Since then, it has delivered high-quality performances that are enjoyed by the local community as well as the visitors of Kennebunkport. This old building has witnessed the dawn of the 19th century in this quaint town and will remain present to see centuries more.

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2. Check Out Dock Square

Dock Square is a beautiful historic neighborhood that is conveniently located right in the heart of Kennebunkport. It is a place you should not miss when visiting this delightfully alluring New England town. Take a leisure walk down Ocean Avenue and marvel at the sailboats and fishing boats moored at the docks along Kennebunk river. The picturesque view will take you back to a time when life was simpler and easier.

While enjoying the Atlantic breeze, you can also indulge in a sumptuous meal at a local restaurant or enjoy window-shopping in this magical coastal town. The downtown streets are known for their quintessential shops that offer an array of merchandise that you can use while in town or bring home as a remembrance for your travel.

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3. Check Out The Seashore Trolley Museum

Check out the Seashore Trolley Museum, and maybe even take a ride on one of the trams that go back to the early 1900s. The Seashore Trolley Museum is the first and largest mass transit museum in the world. It boasts a massive collection of vintage trams, automobiles, and buses that have been maintained and restored to its former glory. In 1980, ten of these trams earned their rightful position in the National Register’s list of Historic Places.

The Atlantic Shore Line Electric Railroad used to be the major mode of transport back in the 1800s. Today, it serves as a demonstration railway and a monumental tourist attraction that people can enjoy when visiting the Seashore Trolley Museum. 

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4. Do a Beer Tasting of the Local Brew

If you love a good craft beer, then don’t miss doing some flights of beer at all the local favorite breweries. Directly beneath Federal Jacks Restaurant, you will find their seven barrel brewery, Kennebunport Brewing Company. Not only can you take a tour of the facilities, but you can also choose the sampler where you will be tasting beers with names like Old Thumper and Fuggles. Who could resist? Batson River Brewing has their flagship location in downtown Kennebunk, Maine and Sebago Brewing Co. is another local favorite. 

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5. Eat a Blueberry Pie

The whoopie pie is the official state treat of Maine, but the blueberry pie is the official state dessert. During the peak season you will see this fruit featured in many restaurant dishes, like blueberry barbecue ribs or blueberry cornbread. But, there’s nothing like a homemade bubbling blueberry pie hot from the oven. Mabel’s restaurant is not only a place for a killer lobster roll, but they also serve a scrumptious blueberry pie a la mode. Another contender is Alisson’s in Dock Square.

If you don’t want to wait for pie until your visit, then make your own with this Maine Wild Blueberry Pie recipe

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6. Eat a Lobster Roll

It doesn’t get much more quintessential Maine than eating fresh lobster, and one of the best is at The Clam Shack. Their lobster roll, simply made with fresh lobster meat, mayonnaise, and melted butter, warrants the dozen people deep line that commonly forms in front of their order window. This $17.95 sandwich is stuffed with a whopping one pound of fresh lobster meat and has been mentioned in everything from Gourmet magazine to the New York Times. No surprises there, because it is amazing.

Though The Clam Shack is truly delicious, many of the locals also swear by Port Lobster or Mabel’s to get their lobster roll fix. You may just have to do a lot of research (lobster roll sampling) to find your favorite. Bummer.

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7. Eat a Whoopie Pie

The Whoopie Pie is a delightful dessert that has two pillowy chocolate cakes (cookies) sandwiched around a sweet frosting filling—an Oreo on steroids. Originally, these treats were made from leftover cake batter, but now their popularity warrants their own recipe and nonstick pan. Though the origin of the whoopie pie has been a battle between Pennsylvania and Maine, the latter of the two has claimed it as the official state treat. And what a treat it is.

You can stop into HB Provisions, an inviting general store where the Bush clan have been known to frequent, to test their version that is truly delicious. Or just make your own with this Old-Fashioned Whoopie Pie Recipe.

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8. Eat an Exotic Flavored Ice Cream

Each day Rococo Artisan Ice Cream has fourteen delectable flavors in their rotation. You can indulge in a scoop of traditional chocolate, but for this bucket list check you must order a more creative cone. Though the Goat Cheese & Blackberry Chambord Swirl is delightful and the Spicy Rocky Road will give you tongue a divine kick, why not give the Sweet Avocado Cayenne a shot? Or how about the Sunfish Wheat Ale Beer with Candied Ginger & Apricots. Head into their shop and select the most unique flavor they have that day! 

What are the craziest ice cream flavors in America? Find the answer here.

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9. Go to the Beach

With its convenient position on the Atlantic Seaboard, this town offers a lot of opportunities for enjoyment and relaxation that every beach lover can take delight in.   

• Parsons Beach: Parsons Beach is the perfect option for those who are looking for a more private beach experience. Although parking is limited and permission is required to access this open beach, it is still worth the visit to enjoy a scenic walk in this untainted nature.
• Kennebunk Beach: Kennebunk Beach is a great choice to swim, kayak, and enjoy a whole day of a picnic while enjoying the Atlantic breeze. If you’re looking for the best beach to spend quality time with your family.

• Goose Rocks Beach: Goose Rocks Beach is without a doubt the most agreeable option for you. Little children can safely swim and play in its well-maintained shore while enjoying the tiny waves.

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10. Take a Food Tour 

There is no better way to travel than to combine your trip with gastronomy. Join the Maine Foodie Tour to enjoy the exquisite taste and the culinary history of Kennebunkport. This tour is in itself a popular tourist attraction taking the visitors through a half-mile culinary journey starting from the Dock Square to the lower village of Kennebunkport. Savor on those delightful lobsters and chowders while chatting with the local food artisans who help keep Maine’s centuries-old culinary tradition.

Got a dog? Kennebunkport is a dog-friendly town! You can bring your pooch to the beach, buy them designer gear at one of the many shops, sleep with them at a friendly Inn and even take them on a doggie food tour—a perfect addition to your dog bucket list. Maine Foodie Tours will accompany you and your four-legged friend on a “doggy and me” tour featuring treats for the both of you. 

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11. Spend the Afternoon in Cape Porpoise 

Spending an afternoon filled with light adventure and discovery is easy in Cape Porpoise. It is a quiet fishing village where many lobster boats unload their daily catch and the lighthouse is the most known landmark. However, there are also far more things to do too. You can rent bikes to cruise the country roads or rent a kayak to explore the water views. 

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12. Kayak the Kennebunk River

Get a different perspective of the Kennebunk’s by kayaking along the picturesque tidal river. This working river is a major part of the economy and local culture, which you can experience from the water. At Coastal Maine Kayak you can choose to take one of their Kennebunk river tours or opt for a self-guided kayak adventure.

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13. Rent Vintage Bikes from Coastal Maine Kayak

Traveling in this magical seaside town will only be complete if you pedal its coast in style. Coastal Maine Kayak offers a large selection of new and vintage bicycles for beach cruisers of all ages. Aside from vintage bikes, they also offer new bike models that come in different sizes, styles, and features that can suit your biking requirement. Whether you plan to go biking alone or along with friends, children, or even your pets, there is a bike that is suitable for you to enjoy an absolutely fun outdoor activity.

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14. See Walker’s Point

The Walker’s Point Estate located on Ocean Avenue is the summer home of former President George Bush and his family. The central house of the estate was built using the colonial American architectural style common in the New England region since the 1600s. It is a popular landmark that celebrates the rich history of New England. Although tourists are not allowed in the estate, visitors can stop their vehicle and take advantage of the vantage point from Ocean Avenue to enjoy the amazing architecture and the beautiful nature that surrounds it.

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15. Sleep in a Historic Bed and Breakfast

Historic Bed and Breakfasts are plentiful in the coastal town of Kennebunkport. But, which one will you choose? One of the best, and the one that I called home for a few lovely nights, is Captain Lord Mansion. This authentic shipbuilder’s mansion can be found in a quiet residential neighborhood, just a block from the beach and a few minutes from Dock Square.

Other Favorite Inns: The White Barn Inn, Captain Jefferds, 1802 House and Maine Stay

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16. Try to Spot a Celebrity

Kennebunkport sees its fair share of celebrities, besides the Bush family and other dignitaries. It is a secret getaway to many of the famous. You may see them eating lobster rolls at The Clam Shack, sleeping at the luxurious White Barn, having a cup of coffee at HB Provisions or catching a play at the nearby the Ogunquit Playhouse. *Remember that they are probably enjoying a quiet getaway, so try not to disturb them!

Some of the celebrities rumored to sneak off to the Kennebunks are Taylor Swift, Quentin Tarantino and Billy Joel.

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17. Take a Lobster Boat Cruise

You have eaten your lobster roll(s), now get a glimpse into the life of a lobster fisherman. The Rugosa Lobster Tour will take you on a one and a half hour scenic tour of the Kennebunk River in a classic New England wooden lobster boat. On this cruise, you can get your hands dirty (if you choose) while assisting in the hauling of the lobster traps. 

If a more relaxing cruise is what you seek, then sail with Schooner Eleanor Sailing Cruises who will take the schooner along the beautiful Kennebunks coastline. This is an experience that will have you feeling like a millionaire yachter on a boat that is a beautiful example of fine local craftsmanship.

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18. St. Ann’s by-the-Sea Episcopal Church

St. Ann’s Episcopal Church is worth the visit even if you don’t plan on staying for service. The church grounds include a beautiful stone chapel, seaside chapel, columbarium and rectory. The picturesque Stone Chapel is the main draw for visitors, and it’s no wonder. The interior and exterior is made with breathtaking sea-washed stones, instead of wood and the stained glass windows date back to the late 1800s/early 1900s.

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19. Visit Goat Island Lighthouse

Goat Island lighthouse is situated off Cape Porpoise and is one of the most popular tourist attractions in New England. The tower was built in 1833 to serve as a beacon light for mariners. When President George H.W. Bush took the office starting 1989 to 1993, the lighthouse served as a watchtower for some of his Secret Service agents. The Walker’s Point Estate is conveniently visible when viewed from the top of the tower.

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20.Visit Rachel Carson Wildlife Refuge

Rachel Carson Wildlife Refuge is a 9,125-acre sanctuary along the southern coast of Maine. The center was established in 1966 and was named after Rachel Carson, author, and marine biologist. It is dedicated to preserving the natural habitat of the different wildlife in the area, including migratory birds. The sanctuary also features a trail where visitors can walk and exercise while learning about the different flora and fauna that take refuge in this massive piece of land.

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Essential Tips for Visiting Kennebunkport, Maine Getting There: Portland International Jetport is a major hub and most airlines will fly into it. You can easily check for the best fare deals at Skyscanner, which also has the option to choose ‘cheapest month’ as the departure to find the lowest priced dates to fly to your destination. It is a 30 minute drive from the airport to Kennebunkport, so you could book a rental car with RentalCars.com, or you could take a taxi, Uber, or Lyft. Where to Stay in Kennebunkport: It’s best to stay near the city center, public transportation or the area that you will be spending the most time in. I stayed at Captain Lords, which was perfect, but there are plenty of other options.  The Lodge at Turbat’s Creek (moderate), or Franciscan Guest House (moderate) are great choices in Kennebunkport. For something on the less expensive side, try the Footbridge North Hotel located in Wells. For a hotel with a little more extravagance, book a room at Captain Jefferds Inn (luxury). Or search some great deals on hotels of your choice at Booking.com. If you’re looking for more of a home atmosphere (or are traveling with a group of people), head over to Airbnb that has houses, apartments and even just a room for rent in every price range.  Getting Around: Renting a car in Kennebunkport is the best way to really experience the area and RentalCars.com has some great deals. If you are not renting a car, there are plenty of options. A popular way to get around is with Kennebunkport’s Sightseeing Trolley. Kennebunkport is also surprisingly easy to navigate by foot or bicycle. Taxis, Lyft and Uber are also available all over the city. Best Tours in Kennebunkport: You can find some of the top tours at Get Your Guide or Viator, and here are some of the top ones: Lunchtime Culinary Walking Tour2-Hour Historical Walking TourRugosa Lobster Tours  Schooner Eleanor Sailing Tours

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