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Kennebunkport, Maine 3 Day Travel Itinerary

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Harbor |  Kennebunkport Maine 3 Day Travel Itinerary
Kennebunkport Waterfront

Kennebunkport is a Maine coast vacation destination with three neighborhoods to explore: Kennebunkport, Kennebunk, and Cape Porpoise. Our 3-day Kennebunkport, Maine travel itinerary will help you enjoy all the area’s attractions and things to do.

Legendary for its ship building history, Kennebunkport remains a working port for leisure yachts and lobster boats. Visitors will be charmed by the region’s quaint inns, art galleries, and New England coast eateries. Let us introduce you to the best things to do in Kennebunkport Maine.

Marina Dinghies | Kennebunkport Travel Itinerary | Southern Maine Coast
Marina Dinghies

Kennebunkport is a 4-season New England travel destination. Businesses change opening hours and days seasonally. Always check ahead to confirm your plans. Also, to best enjoy the region we recommend utilizing a personal vehicle or rental car as public transit is sparse.

Kennebunkport Maine Hotels

In Kennebunkport you will find a range of lodgings from B&B's in old captain's houses to luxury resorts to affordable chain options. Check out Kennebunkport hotels here.

Kennebunkport 3 Day Travel itinerary At A Glance | Things to do in Kennebunkport Maine
Colony Hotel | Kennebunkport's Ocean Avenue | Maine Coast Travel Destination
Colony Hotel | Ocean Avenue

For more information on Maine Coast travel destinations read our articles on:

Lobster Traps | Kennebunkport Travel Itinerary | New England Coast
Lobster Traps | Kennebunkport

Day 1: Explore the Dock Square, Historic District, and Harbor of Kennebunkport Maine

The village of Kennebunkport is full of New England style capes and colonials perched upon the harbor and river. Take some time to wander the narrow streets of this lovely beach town.

Begin your exploration at the intersection of Summer Street and Western Ave. Walk across the Kennebunk River to Dock Square. Then, get to know town by wandering the restaurants and shops of the narrow streets between Maine Street, Ocean Avenue, and the Village Green.

Dock Square Kennebunkport | Maine Coast Vacation
Dock Square

Later in the day, learn about the region’s rich colonial and ship building past with a walking tour of Kennebunkport’s historic district. View colonial churches and the elegant homes of sea captains and wealthy merchants.

Or, if you would rather be out on the water, book a cruise along the Maine coast. From Dock Square you can book lobster boat tours, sailing excursions, whale watches, and fishing charters.

Boat Charters | Kennebunkport Things To Do | New England Travel
Boat Charters Kennebunkport

Spend the evening in Kennebunkport. A night at Federal Jacks is always fun. Do a Kennebunk Brewing Company brew tour on the first floor; then, head upstairs for dinner with great water views. Or, try the Pilot House, serving fresh seafood, and often live music. For a fun twist, tray a local ghost walking tour.

Federal Jack's Restaurant | Kennebunkport Restaurants | Maine Coast
Federal Jack's and Shipyard Store

Day 2: Explore Shore Walk, Walking Tour, Ocean Avenue, and Cape Porpoise

Begin the day with a brisk hike on the 2-mile Parson’s Way Shore Walk. The trail begins at Arundel (Colony) Beach and passes by Sprouting Rock and Blowing Cave, St. Ann’s Church, Walker Point, grand summer “cottages,” and the cliffs of the Ocean Avenue coast.

Outdoor Alter | Parson's Way Shore Walk | Kennebunkport Things To Do
Outdoor Alter | Parson's Way Shore Walk

At lunchtime, walk downtown to sample some of Kennebunkport’s 5-star food scene. The town is home to some of the regions most celebrated chefs. Sample chowders, desserts, lobster, and inventive spins on regional favorites as you trek through the village.

After lunch, take a scenic drive past some of Maine’s most stunning scenery. From Kennebunkport, take Ocean Avenue past the grand old resorts, like the Nonantum and Colony, to the palatial summer “cottages” on the outskirts of town.

St. Ann's Episcopal Church |Ocean Avenue | Kennebunkport Travel
St. Ann's Episcopal Church

Stop along the route at the magnificent St. Ann’s Episcopal Church. This rustic church has landscaped grounds and a commanding view of the southern Maine coast. The church and outside alter may be visited if open and not in use.

Further along Kennebunkport’s Ocean Avenue is the Walker Point Estate. The estate, or “Bush Compound,” is the summer home of the dynastic Bush family. There is a memorial to George “H” at one of the lookouts.

Walker Point Estate | Bush Compound | Kennebunkport Itinerary | Southern Maine Coast
Walker Point Estate | Bush Compound

Continue your drive to the village of Cape Porpoise. Though only about 3-miles from Kennebunkport, the working lobstering and fishing community feels a world away. Walk the pier to view the Goat Island Lighthouse. There are several restaurants and lobster shacks in the area selling fresh seafood. Drive the surrounding country-side for scenes of down east coastal life or take a kayak paddle around the harbor.

This evening, drive a half-hour north to the city of Portland. Walk the Portland Old Port and check out its famed brewery scene with a bus tour of local breweries.

Maine Coast | Things to do in Kennebunkport Maine | New England Coast
Maine Coast

Day 3: Shop Kennebunk’s Downtown. Relax at Goose Rocks Beach.

Drive 5-miles to the town of Kennebunk. Like its neighbor, Kennebunk is full of fun shops, cafes, antique shops, and art studios. Park by the small park by Mousam River, and walk Main Street. Have lunch at the charming Kennebunk Inn Tavern.

The Kennebunk Inn | Kennebunkport Itinerary | New England Travel
The Kennebunk Inn

Next, head for Kennebunkport’s Goose Rocks Beach. A 15-minute ride from Kennebunk, the 3-mile beach is known for its white sand and gently rolling waves. In season, a sticker can be purchased at the Goose Rocks Beach General Store for parking. There are no refreshments or restrooms at the beach. However, across the street from the beach the Tides Restaurant can feed you, and provide facilities.

Marina Ocean Avenue | Kennebunkport Travel Itinerary
Marina, Ocean Avenue

Hope you enjoyed the sun, surf, and “summer cottages,” Laura and Randy

For more information on Maine Coast vacation destinations read our articles on:


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