History and Harbors

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  • 6 Days
  • 2024 DatesJuly-Oct
  • Difficulty LevelEasy
History and Harbors

Discover Maine's Heritage and Scenery: A Summer Feet 6-Day Walking Tour

Maine, first explored in the early 1500s, is steeped in a rich and diverse history. Our 6-day easy walking tour is designed to give you a comprehensive insight into Maine’s captivating past, its distinctive architecture, and its breathtaking natural beauty.

This tour begins in the charming city of Portland, known for its well-preserved historical buildings and vibrant cultural scene. As you stroll through the city, you’ll witness a blend of historic and modern architecture alongside picturesque waterfront views.

Next, the tour takes you to the heart of Maine’s mid-coast, an area celebrated for its quintessential New England beauty. Here, you’ll explore quaint coastal towns, each brimming with character and stories that echo Maine’s maritime heritage.

The tour’s highlight is undoubtedly the stunning Acadia National Park, an area of matchless natural beauty. You’ll be treated to panoramic views of rugged coastlines, pristine forests, and serene mountain landscapes. The park’s beauty showcases the untouched side of Maine, making it a perfect finale for your 6-day exploration.

Join us on this walking tour to experience the unique charm, rich history, and natural splendor of Maine, from Portland’s bustling streets to Acadia’s tranquil trails.

If you have any questions, please get in touch

(Want to explore more multi-day New England tour options? Check out our Cycling Trips in Maine.)

What's Included

  • Five nights’ lodging
  • 4 Dinners, 3 Lunches, 5 Breakfasts
  • Hotel, Meal and Activity Gratuities
  • Experienced Leaders
  • Van Transport
  • Snacks and Beverages
  • Park Entry Fees
  • Souvineer Waterbottle and T-Shirt


  • Discover Portland, Maine
  • Hike the Maine Coast
  • Enjoy Fresh Seafood
  • Explore Acadia National Park

Pick Up/Drop Off

Portland, Maine (PWM)

2024 Dates

September 22-27
October 6-11



$ 3595.00 per person

Single Supplement $900.00


Day 1Discover Portland

Meet your guides in the early afternoon in Portland. Founded in 1623, and full of charm you enjoy a guided walk through Portland’s historic West End and a visit to the Portland Head Light before our welcome dinner.

Day 2Freeport, Damariscotta, and Pemaquid Point

Known as the home of L.L. Bean, Freeport is much more than shopping, we enjoy an easy stroll through the woods and along the shore of Wolfe’s Neck State Park.  After a short drive, we pause for you to enjoy lunch on your own and to explore the town of Damariscotta. before an afternoon walk through the Dodge Point Preserve. Here we follow old farm roads through mixed forests to the shore of the Damariscotta River. Our path along the river offers a great opportunity to spot a variety of shorebirds.  A short drive takes us to the Pemaquid Point Lighthouse where we enjoy wine and cheese overlooking the ocean.

Day 3Owls Head Light, and the Rockland Breakwater

In the morning you visit the Owl’s Head Light before walking the mile-long breakwater in Rockland Harbor for great views of Penobscot Bay and Rockland Harbor. After some time explore Rockland and enjoy lunch it is a short drive to Camden where enjoy a ride on an antique wooden schooner.

Day 4Camden Hills and Castine

Your morning begins with a hike in Camden Hill State Park for views of Lake Megunitcook, Penobscot Bay and the opportunity to see the sweeping panorama of the Maine Coast all the way to Acadia National Park.  In the afternoon we visit Castine, one of the most historic towns in Maine. Castine has flown the flag of four nations in its rich history. Enjoy a walking tour of the town and the monuments to early struggles for control of the new world.

Day 5 Schoodic Head

Today you travel to the quiet part of Acadia National Park the Schoodic Peninsula.  You hike the Buck Cove Mountain Trail for wonderful views of the ocean and Acadia National Park.

Day 6 Cadillac Mountain

The highest peak on the Eastern Seaboard between Maine and Rio, Cadillac is the first place in the United States to see the sunrise. We will drop you where the trail crosses the park loop road so you can walk the last mile to the summit. Enjoy views of Frenchman Bay and the Porcupine Islands. A noon departure takes you back to Portland

  • Hiking: 1 mile
  • Meals: Breakfast


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