Exploring the Best of Maine: A 3-Day Scenic and Culinary Adventure from Shirley, NY

Day 1: Portland Discovery

Portland, Maine on May 18, 2025

7:00am

Drive from Shirley, NY to Portland, ME

Start early for the approximately 5.5-hour drive to Portland to maximise your day exploring Maine's largest city.
USD 0, 5h30m

12:30pm

Breakfast at The Holy Donut

Enjoy unique, handmade potato doughnuts with a variety of flavours for a light but delicious start.
USD 10, 45m

1:30pm

Walk Old Port Waterfront

Explore the charming cobbled streets of Portland’s Old Port district, filled with boutiques, galleries, and historic buildings.
USD 0, 1h30m

3:00pm

Visit Portland Head Light

Tour Maine’s oldest lighthouse offering stunning coastal views; perfect for photos and a peaceful stroll along Fort Williams Park.
USD 0, 1h

5:00pm

Dinner at Eventide Oyster Co.

Sample fresh local oysters and Maine seafood in a lively atmosphere; a must-try for seafood enthusiasts.
USD 40, 1h30m

7:00pm

Relax at your Portland accommodation

Rest and prepare for the next day’s adventure to Acadia National Park.
USD 0, overnight
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Day 2: Acadia National Park

Bar Harbor, Maine on May 19, 2025

7:30am

Breakfast at Becky’s Diner

Enjoy classic American breakfast options in this local favourite known for generous portions.
USD 15, 45m

8:30am

Drive to Acadia National Park

Travel from Portland to Bar Harbor, the gateway to Acadia National Park, approx 3 hours.
USD 0, 3h

11:30am

Explore Acadia National Park

Visit main highlights such as Cadillac Mountain, Jordan Pond, and the Ocean Path trail for breathtaking views and nature walks.
USD 35 (park entry fee per vehicle), 4h30m

4:00pm

Lunch at Jordan Pond House

Famous for its popovers and tea with a view over Jordan Pond, a relaxing spot to refuel.
USD 25, 1h

5:30pm

Explore Bar Harbor town

Stroll through the quaint downtown with shops, art galleries, and cafes.
USD 0, 1h

7:00pm

Dinner at 2 Cats Restaurant

Enjoy seafood and American cuisine with harbour views, a great way to end your Acadia day.
USD 40, 1h30m

9:00pm

Stay overnight in Bar Harbor

Relax after a busy day surrounded by natural beauty.
USD 0, overnight
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Day 3: Coastal Towns & Return

Camden, Maine / Travel to Shirley, NY on May 20, 2025

7:30am

Breakfast at Jeannie's Great Maine Breakfast

Treat yourself to homemade pancakes and local fare in this welcoming spot in Bar Harbor.
USD 15, 45m

8:30am

Drive to Camden

Head south to the beautiful harbour town of Camden, about 1.5 hours drive.
USD 0, 1h30m

10:00am

Explore Camden Hills State Park

Hike to Mount Battie summit for spectacular views of Penobscot Bay and Camden harbour.
USD 4 (parking fee), 2h

12:30pm

Lunch at Long Grain

Asian fusion cuisine offering fresh and creative dishes, a local dining gem.
USD 30, 1h

1:30pm

Explore Camden town centre

Visit local shops, galleries, and enjoy a stroll around the waterfront.
USD 0, 1h

2:30pm

Begin drive back to Shirley, NY

Set out on the approximately 6.5-hour drive back home, stopping as needed.
USD 0, 6h30m
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