The Best Things To Do In Quaint Kennebunkport: Where To Eat, Stay, And Play

destinations, maine, united states, the best things to do in quaint kennebunkport: where to eat, stay, and play

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Kennebunkport is synonymous with one thing: the Bush compound. During the time when George H. W. Bush was president, from 1988 to 1992, Kennebunkport became a household name. It was known as the Summer White House, the family estate where the president would spend time during the summer.

But Kennebunkport is so much more than just the summer home of the Bush family — it’s one of Maine’s most fantastic ocean communities (actually two communities — Kennebunk and Kennebunkport, often referred to as “the Kennebunks”), and there’s much to see and do.

Here’s what to add to your must-do list when you visit.

destinations, maine, united states, the best things to do in quaint kennebunkport: where to eat, stay, and play

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Check Out Dock Square

This is what most people picture when they think of Kennebunkport. Those famous photos of the 41st president walking around Kennebunkport, flanked by the Secret Service, were taken in and around the Dock Square area downtown. Remember, there’s Kennebunk and then there’s Kennebunkport, and this is Kennebunkport.

The harbor here is a wide portion of the Kennebunk River as it makes its way to the Atlantic Ocean. When you stand on the bridge over the river, you’re a little less than a mile from the ocean by boat. This was the center of Kennebunkport’s shipbuilding industry years ago, but now the area caters to tourists.

Make sure you check out both sides of the bridge. There are shops, restaurants, and art galleries on both the east and west sides of the harbor. And if you want to take a sightseeing cruise out on the ocean, this is the spot to find one. You’ll find several boats to charter here as well as many deep-sea fishing excursions.

destinations, maine, united states, the best things to do in quaint kennebunkport: where to eat, stay, and play

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Visit Goat Island Lighthouse

Maine is famous for its rocky shores. And it’s not just the shoreline — Maine has many small islands just off the coast. Because of this, many lighthouses had to be built to guide ships around the coastline. And the most famous lighthouse in the Kennebunkport area is the Goat Island Lighthouse.

The best place to view the Goat Island Lighthouse is from the Cape Porpoise Pier. If you take Pier Road from Highway 9, it will dead-end right at the pier. From there, you can get the best view of Goat Island Lighthouse out in the ocean.

Or, even better, you can book a tour on a boat that will take you out to Goat Island to see the lighthouse up close. This is a great way to appreciate the area. Get out on the ocean, see Kennebunkport’s shores from the water, and end up on the island with the lighthouse. Tours can be booked through New England EcoAdventures, operating right out of the harbor in Kennebunkport.

Check Out The Seashore Trolley Museum

Clang, clang, clang went the trolley

Ding, ding, ding went the bell

You don’t have to Meet Me in St. Louis to see the famous Trolley Museum — the museum is located in the Kennebunks. Take Log Cabin Road to the north, and you’ll come to the Seashore Trolley Museum just north of town.

This is an indoor-outdoor museum, so try not to visit on a rainy day. Here you will find trolleys galore, many of them restored to their original glory. You could spend an entire afternoon here learning about the history of trolleys in the United States.

destinations, maine, united states, the best things to do in quaint kennebunkport: where to eat, stay, and play

Yingna Cai / Shutterstock

See Walker’s Point

Walker’s Point is the famous peninsula where the Bush compound is located. You can’t tour the compound, of course — the Secret Service might have something to say about that — but many visitors to the area do want to see where the compound is located.

Right across from Cape Arundel, you will see a skinny peninsula with several homes on it. That entire peninsula is Walker’s Point; it has a long history dating to the late 1800s, when Dorothy Walker married Prescott Bush, and Dorothy’s father built them a house on Walker’s Point. Prescott’s son George — the 41st president — eventually purchased the property and, when he became president in 1989, Walker’s Point became a meeting place for world leaders.

From downtown Kennebunkport, follow Ocean Avenue out to Cape Arundel. As you wrap around Cape Arundel, you’ll see a pull-off on the right (just past Endcliffe Road) with a small memorial to George H. W. Bush. From that pull-off, you can see all of Walker’s Point right in front of you across the water.

Walk Around Kennebunk

Remember, “Kennebunkport” is generally used to describe the entire area, but within the area are both Kennebunkport and Kennebunk. To make it even more confusing, Kennebunkport sits on the Kennebunk River, but Kennebunk is located on the Mousam River.

The best place to start your visit to Kennebunk is at Rotary Park near the intersection of York Street and Water Street. From there, you can see several of the small waterfalls in the Mousam River. You can walk the downtown area in both directions from there, with York Street being the center of it all. Kennebunkport might be the most famous, but Kennebunk has its own charm. You can’t visit the area without seeing both!

destinations, maine, united states, the best things to do in quaint kennebunkport: where to eat, stay, and play

Robert Rosenthal

Get A Photo Of The Sunset From Lanigan Bridge

This was probably the best view of our trip. My wife and I had dinner in Kennebunkport on the west side of the Lanigan Bridge. Then we walked across the bridge to the east side of the harbor to check out the shops (and to grab some ice cream). Our car was at the restaurant, so right at sunset, we walked across the bridge back to our car. That’s when I took the photo above.

The photo doesn’t even show any of the main harbor. The sailboats and fishing boats are all moored on the other side of the bridge. But the view — the sunset to the west and the bridge and boats to the east — was just spectacular.

destinations, maine, united states, the best things to do in quaint kennebunkport: where to eat, stay, and play

Yingna Cai / Shutterstock

Where To Eat In Kennebunkport

We stopped at several restaurants in Kennebunkport. These were our favorites.

Federal Jack’s Restaurant And Brew Pub

We sat upstairs at Federal Jack’s, out on the deck, and enjoyed the views of the harbor. The restaurant is attached to Kennebunkport Brewing Company, so make sure to sample their beers. Try the clam chowder as well — you are right next to the ocean, after all.

Duffy’s Tavern & Grill

Duffy’s Tavern & Grill is located in Kennebunk, inside the old mill and right next to the waterfall. There’s so much history to experience here. The food is your typical bar fare, so Duffy’s would be a great spot to stop for lunch as you’re walking around Kennebunk.

The Boathouse Restaurant

There are restaurants near the harbor in Kennebunkport, and then there’s The Boathouse. If you like sitting outside next to water, this restaurant is for you — you’ll feel like you’re sitting out in the harbor. When we were there, there was a large sailboat docked just across the harbor — it felt like the sails were looming over us as we ate. It was awesome. And the food was great, too.

Where To Shop In Kennebunkport

There are two main shopping areas, one in Kennebunk and the other in Kennebunkport. In Kennebunkport, the shops center on Dock Square and are located on both sides of the bridge. The best place to start is at the intersection of Highway 9 and Ocean Avenue. But don’t forget about the secondary street across the bridge and up the hill. If you turn to the right off of Highway 9 onto Beach Avenue, you will find several more blocks of shops and art galleries to enjoy.

The second main shopping area is in Kennebunk. Please note that you can’t easily walk from one shopping area to the other — they’re more than 4 miles apart. You’ll take State Route 35 out of Kennebunkport to get to Kennebunk. Once there, check out all of the clothing stores and knickknack shops along Main, York, and High Streets.

Where To Stay In Kennebunkport

The single best place to stay if you want to be at the heart of it all is at The Boathouse, mentioned above. The Boathouse is a restaurant, but it’s also a hotel. And it’s located right in the heart of Kennebunkport. Everything in Kennebunkport, including Walker’s Point, can be easily reached on foot from The Boathouse.

For an authentic Maine experience, check out the Captain Jefferds Inn. This bed and breakfast is located in an old sea captain’s home right in the heart of the historic district. The historic district covers the hillsides above the Dock Square area, so you’ll be right in the middle of the action. If you’re looking for charm, this is your place.

What To Know Before You Go

Some vacationers like to find a place to stay right in the heart of town so that they don’t have to rent a car. They just need to find some form of transportation from the airport to the hotel, and then they walk to everything for the rest of the trip.

Kennebunkport really isn’t that kind of place. If you stay in the downtown Kennebunkport area, it could be done. But there’s so much to explore in and around the area that you’re going to want a car.

And that’s not just so you can travel from Kennebunkport to Kennebunk. This area is home to some of the most beautiful drives you’ll ever experience. Check the map for oceanfront drives and head to the north or the south — you’re bound to encounter some incredible ocean views.

For more to see and do in beautiful Maine, visit this page.

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