In Kennebunkport, Maine, Santa arrives by lobster boat every December

Maine’s coast doesn’t get more classic than this

Ninety miles north of Boston, where the Kennebunk River meets the Atlantic, a small Maine town has been pulling people in for over a century.

Rocky shorelines, sandy beaches, a presidential compound perched on an ocean point, and a trolley museum that shouldn’t exist but does. Come in summer and the harbor hums.

Come in December and Santa arrives by lobster boat. Either way, the town earns the trip long before you reach the waterfront.

From fishing settlement to shipbuilding powerhouse

Europeans first put roots down here in 1653, calling the place Cape Porpoise.

Conflict with Native Americans pushed them out, and the settlement was reorganized in 1719 under the name Arundel.

After the Revolutionary War, the town turned into a serious shipbuilding center, sending hundreds of vessels out of its harbor through the 1800s.

In 1821, it was renamed Kennebunkport to draw more trade, trading on the Kennebunk River’s already solid reputation as a shipping route.

When shipbuilding faded, wealthy New Englanders moved in with their summer cottages.

Many of those grand homes still stand today, and the Kennebunkport Historic District holds a spot on the National Register of Historic Places.

Dock Square is where everything starts

Dock Square sits where the Kennebunk River meets the village center, and it’s the place most people find first. Family-owned shops line the square alongside galleries and restaurants.

You can grab a lobster roll and watch boats move up and down the river without going more than 50 feet from your car. It’s also the launch point for trolley rides, walking tours, and scenic drives along the coast.

In early December, the square transforms into the center of the town’s Christmas Prelude festival, but more on that later.

The Bush family’s ocean compound on Walker’s Point

Since the early 1900s, Walker’s Point has been the Bush family’s summer address.

George Herbert Walker bought the rocky ocean property in 1902, and when his grandson became the 41st president, the estate became the Summer White House from 1989 to 1993.

Margaret Thatcher and Mikhail Gorbachev both came here for meetings.

The property is private, but you can see it from a public overlook on Ocean Avenue near Blowing Cave Park. A monument called the Anchor to Windward, honoring President George H.W. Bush, stands just down the road.

Walk Ocean Avenue all the way to the Bush estate

Parsons Way is a two-mile paved path that follows Ocean Avenue along the shoreline, and it’s worth every step.

It begins near Colony Beach and winds past rocky outcroppings, crashing surf, and some of the grandest seaside homes in southern Maine.

Along the way, you’ll pass Spouting Rock and Blowing Cave, where the ocean forces itself through gaps in the rock with enough energy to send water shooting up.

St. Ann’s Episcopal Church, built from stone with stained glass windows facing the water, sits along the route. The path ends near Walker’s Point.

The trolley museum the whole world didn’t know it needed

The Seashore Trolley Museum didn’t start with a grand plan.

In 1939, a group of rail fans rescued a streetcar from the Biddeford and Saco Railroad before it got scrapped. That rescue turned into the world’s first and largest museum of mass transit vehicles.

Today the collection tops 250 cars from the United States, Canada, Australia, Japan and Europe.

You can ride a restored antique trolley along a heritage railway that follows part of the old Atlantic Shore Line route. A glass-walled restoration shop lets you watch the work happening in real time.

Ten of those vehicles carry National Register status.

Cape Porpoise runs on lobster boats and salt air

A few miles from Dock Square, Cape Porpoise feels like a different era. This is a working fishing village where lobster boats come in and go out all day.

There’s a small general store, a handful of waterfront spots serving fresh seafood, and a public pier where you can stand and look straight out at Goat Island and its lighthouse. The crowds that fill Dock Square in summer thin out here.

If you want a sense of what coastal Maine looked like before the resort era arrived, this is the place to find it.

The lighthouse that Secret Service agents once called home

Goat Island Lighthouse has watched over Cape Porpoise Harbor since 1833. The tower standing today was built in 1859, rises 25 feet, and flashes white every six seconds.

Maine kept a keeper on the island longer than almost anywhere else, finally pulling the last one in 1990. During the Bush presidency, Secret Service agents used the island to monitor the sea approach to Walker’s Point.

The Kennebunkport Conservation Trust has managed the lighthouse since the early 1990s and restored it to its mid-century look. In summer, you can dock a boat at high tide, and guided tours sometimes run.

Pick your beach and stake your claim

Kennebunkport and its neighbor Kennebunk share a stretch of coastline with enough variety to suit most people. Goose Rocks Beach runs long and flat, drawing families and birdwatchers.

Gooch’s Beach and Mother’s Beach in Kennebunk sit closer to town and fill up fast on summer weekends. Colony Beach, at the mouth of the Kennebunk River, is smaller and quieter.

Parsons Beach is privately owned but open to the public year-round, with no development in sight in either direction. At most area beaches, you’ll need a parking permit during summer months, so plan ahead.

Get out on the water and see how lobsters are caught

Boat tours are built into the rhythm of Kennebunkport.

Lobster boat tours take you out with a working crew so you can watch traps being hauled and handled up close. Whale watch cruises head into the open Atlantic looking for humpbacks, finbacks and minkes.

The Schooner Eleanor sails passengers out of the Kennebunk River and into the ocean on sailing trips that run a few hours. Kayaking and paddleboarding work well on the river and around the Cape Porpoise islands.

Fishing charters can set you up to catch your own dinner if that’s more your speed.

A monastery on the river open to anyone who walks in

St. Anthony’s Franciscan Monastery doesn’t ask much of you.

It sits on 66 acres along the Kennebunk River, just off Beach Avenue, and the grounds are open to visitors of all backgrounds from sunrise to sunset.

Lithuanian Franciscan friars established it in 1947 on a former private estate. English-style gardens follow the riverbank.

Walking paths lead past outdoor shrines and a grotto. The chapel combines traditional and modern design in a setting that looks out over the water.

It’s about a mile from the noise of Dock Square and feels twice that far.

Santa skips the sleigh and arrives by lobster boat

Christmas Prelude started in 1982 as a simple tree lighting organized by local business owners. Four decades later, it runs across two weekends in early December and draws visitors from well outside Maine.

Tree lightings, caroling, craft fairs, fireworks and holiday parades fill the schedule.

The signature moment is Santa coming in by lobster boat on the Kennebunk River, which makes perfect sense for a town built on fishing history.

In Cape Porpoise, a tree constructed from stacked lobster traps gets decorated with lights and buoys. HGTV has ranked it among the top Christmas towns in the country.

Visit Kennebunkport, Maine

You can reach Kennebunkport from Portland International Jetport, about 30 miles north, or from Boston’s Logan Airport, roughly 90 miles south.

The Amtrak Downeaster stops in nearby Wells if you’d rather skip the rental car. Summer runs hot from Memorial Day through Labor Day, with all beaches and boats in full swing.

Fall brings foliage and smaller crowds.

For local history that runs from sea captains to presidents, stop into the First Families Kennebunkport Museum at White Columns, an 1853 Greek Revival home right on Dock Square.

This article was created with AI assistance and human editing.

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