Kennebunkport Travel Guide: Things to Do, Best Time to Visit & Itinerary

Kennebunkport is the definition of New England maritime elegance. For centuries, this village has been a haven for shipbuilders, sea captains, and summer vacationers seeking the curative powers of the Atlantic. The town exudes a sophisticated yet approachable charm, where the salt air mingles with the scent of wild roses and frying clams. It is a place where history is not just preserved in museums, but lived in the Federal-style mansions that line the streets and the working lobster boats that bob in the harbor.

Beyond the postcard-perfect center of Dock Square, the landscape opens up into a dramatic display of nature. From the quiet, sandy stretch of Goose Rocks Beach to the craggy granite shores of Cape Porpoise, the geography here demands to be explored. Whether you are sipping a cocktail on a wraparound porch or navigating a kayak through the tidal marshes, Kennebunkport invites you to slow down and synchronize your rhythm with the tides.

A Legacy of Ships and Presidents

Kennebunkport’s history is deeply rooted in the Kennebunk River, which divides the town from its neighbor, Kennebunk. In the 19th century, this was a shipbuilding powerhouse, launching vessels that traveled the globe. The wealth generated from this industry built the magnificent captains’ homes that now serve as bed and breakfasts and summer residences. Walking down Summer Street is like stepping back into this golden age of sail.

In modern times, the town became globally famous as the summer retreat of the Bush family. Walker’s Point, a rugged promontory jutting into the Atlantic, has hosted world leaders and dignitaries, cementing the town’s place in American political history. Despite this fame, the town retains a small-community feel, where local fishermen and visiting presidents alike share a love for the sea.

The Icons You’ll Want to See

Walker’s Point - This is the most photographed spot in town. Located about 2 miles from Dock Square on Ocean Avenue, the estate offers stunning views of the Atlantic. While the property is private, the overlook on the side of the road provides a perfect vantage point. Free to view.

Dock Square - The commercial hub of Kennebunkport, filled with art galleries, souvenir shops, and restaurants. It is pedestrian-friendly and sits right on the river. Parking is available in municipal lots for approximately $3-$5 per hour.

Goose Rocks Beach - Located 5 miles northeast of town, this barrier reef beach offers 3 miles of soft sand and gentle waves, distinct from the rockier coastline nearby. Parking permits are required in season and cost roughly $30 per day.

Saint Ann’s by-the-Sea - An 1887 stone chapel located just past Walker’s Point on Ocean Avenue. The grounds offer panoramic ocean views and the interior features beautiful stained glass. It is an active seasonal church and open to visitors when services are not in session.

Seashore Trolley Museum - Situated 3.5 miles inland, this is the oldest mass transit museum in the world. Admission is around $13 for adults. It features a massive collection of streetcars from major cities and offers rides on restored tracks.

Planning Your Visit

Getting to Kennebunkport is relatively easy, with the town located just 30 minutes south of Portland International Jetport (PWM) and about 90 minutes north of Boston. A car is highly recommended, as attractions like Goose Rocks Beach and the Trolley Museum are spread out. While the downtown area is walkable, having a vehicle allows you to explore the scenic backroads and neighboring villages like Cape Porpoise.

When packing, remember that the Maine coast can be unpredictable. Even in July, evening temperatures can dip into the 50s, so bringing layers, including a fleece or sweater, is essential. Comfortable walking shoes are a must for navigating the brick sidewalks of Dock Square and the rocky paths along the coastline. If you plan on dining at some of the premier restaurants,