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6-Day Maine Road Trip: Portland to Bar Harbor and Moosehead Lake Adventure

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Day 0: Arrival and Portland Evening

Portland, Maine on June 25, 2025

5:00pm

Arrive at Portland International Jetport

Arrival and car rental pickup, then head to downtown Portland for the evening.
Varies, 0h30m

5:30pm

Check-in at Hotel

Stay overnight at The Press Hotel or Hilton Garden Inn Portland Downtown Waterfront, conveniently located near the Old Port district.
USD150, Overnight

6:30pm

Explore Old Port Waterfront

Walk through the historic cobblestone streets of Old Port, enjoy scenic harbor views, and browse local shops and galleries. Perfect way to enjoy early evening in Portland.
Free, 1h

7:30pm

Dinner at Eventide Oyster Co.

Enjoy fresh oysters and seafood specialties at this popular, highly-rated restaurant, open until 9:30pm.
USD40, 1.5h

9:00pm

Evening Stroll or Craft Beer Tasting

Optional visit to local breweries like Allagash Brewing Company for a late tasting or an evening walk along the Eastern Promenade Trail with views of Casco Bay.
Approx. USD10 for tasting, 1h
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Day 1: Portland to Camden

Portland to Camden, Maine on June 26, 2025

8:00am

Breakfast at The Holy Donut, Portland

Start your day with iconic potato donuts and coffee; open 7am to 3pm.
USD5, 0h30m

9:00am

Drive to Freeport

Short 20-minute drive north to Freeport for shopping and sightseeing.
USD0, 0h20m

9:30am

Shop at L.L. Bean Flagship Store

Explore the iconic L.L. Bean store open 24/7 for outdoor gear shopping.
Free, 1h

11:00am

Drive to Camden

Scenic 1.5-hour drive to Camden along the Maine coastline.
USD0, 1h30m

12:30pm

Lunch at Long Grain, Camden

Waterfront Asian-fusion cuisine, open 11:30am to 9pm.
USD25, 1h

2:00pm

Hike Camden Hills State Park

Moderate 2-hour hike to Mount Battie summit with panoramic views. Park open dawn to dusk. Admission $4.
USD4, 2h

5:00pm

Dinner at Tobias Tavern

Casual American fare using local ingredients, open 4pm to 9pm.
USD30, 1.5h
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Day 2: Camden to Bar Harbor

Camden to Bar Harbor, Maine on June 27, 2025

7:30am

Breakfast at Boynton-McKay Food Co.

Cozy café serving excellent coffee and pastries, opens at 7am.
USD10, 0h45m

8:30am

Drive to Acadia National Park

Scenic 3-hour drive northeast to Acadia National Park.
USD30 park fee, 3h

12:00pm

Lunch at Jordan Pond House

Famous for popovers and tea, open 11:30am to 3pm.
USD20, 1h

1:30pm

Explore Park Loop Road

Scenic drive visiting Sand Beach, Thunder Hole, and Otter Cliffs. Park open dawn to dusk.
Included, 3h

5:00pm

Check-in at Bar Harbor hotel

Rest and prepare for evening activities.
Varies, 0h30m

6:00pm

Dinner at Stewman's Lobster Pound

Waterfront lobster dining open 4pm to 9pm.
USD40, 1.5h
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Day 3: Bar Harbor to Moosehead Lake

Bar Harbor to Moosehead Lake, Maine on June 28, 2025

7:00am

Breakfast at 2 Cats Restaurant

Hearty breakfast to start the day, opens at 7am.
USD15, 0h45m

8:00am

Drive to Moosehead Lake

Approximate 3.5-hour drive northwest to Moosehead Lake region, enjoy scenic views en route.
USD0, 3h30m

11:30am

Check-in and Lunch at Moosehead Lake Lodge

Relax with lake views and enjoy a hearty lunch at the lodge’s restaurant.
USD25, 1h

1:00pm

Moosehead Lake Boat Tour

Take a 2-hour guided boat tour to explore Maine’s largest lake and spot wildlife.
USD40, 2h

3:30pm

Nature Walk on Lily Bay State Park Trails

Explore peaceful forested trails adjacent to the lake, park open dawn to dusk.
USD5, 1.5h

6:00pm

Dinner at The Lakeview Restaurant

Casual dining with regional dishes and beautiful lake views.
USD35, 1.5h
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Day 4: Moosehead Lake to Boothbay Harbor

Moosehead Lake to Boothbay Harbor, Maine on June 29, 2025

7:30am

Breakfast at Moosehead Lake Lodge

Enjoy a fresh breakfast overlooking the lake before departure.
USD15, 0h45m

8:30am

Drive to Rockland

Approximate 3.5-hour drive southeast to Rockland.
USD0, 3h30m

12:00pm

Farnsworth Art Museum Visit

Explore the American and Maine-inspired art collection, open 10am to 5pm.
USD20, 2h

2:00pm

Lunch at Primo Restaurant

Farm-to-table dining with local ingredients, open 11:30am-9pm.
USD30, 1h

3:30pm

Drive to Boothbay Harbor

Short 1-hour drive to charming Boothbay Harbor.
USD0, 1h

4:45pm

Visit Coastal Maine Botanical Gardens

Stroll the exquisite gardens open until 6pm.
USD18, 1h15m

6:15pm

Dinner at The Blue Lobster Grill

Seafood dining with waterfront views, open 4pm-9pm.
USD35, 1.5h
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Day 5: Boothbay Harbor to Kennebunkport

Boothbay Harbor to Kennebunkport, Maine on June 30, 2025

7:30am

Breakfast at The Greenery Café

Cozy spot for coffee and pastries, opens at 7am.
USD10, 0h45m

8:30am

Drive to Kennebunkport

Scenic 1.5-hour drive to Kennebunkport along the coast.
USD0, 1h30m

10:00am

Explore Dock Square

Browse quaint shops, galleries, and cafés in the picturesque town center.
Free, 2h

12:30pm

Lunch at The Clam Shack

Sample classic Maine lobster rolls and fried clams, open 11am to 6pm.
USD20, 1h

2:00pm

Relax at Gooch’s Beach

Spend a relaxing afternoon at a beautiful sandy beach with ocean views.
Free, 1.5h

5:00pm

Dinner at Earth at Hidden Pond

Sophisticated farm-fresh cuisine in an intimate setting, open 5pm to 9pm.
USD45, 1.5h
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Day 6: Kennebunkport to Portland & Departure

Kennebunkport to Portland, Maine on July 1, 2025

7:00am

Early Breakfast at Mornings in Paris

French-style bakery for fresh croissants and coffee, doors open 7am.
USD12, 0h45m

8:00am

Drive to Portland International Jetport

40-minute drive preparing for afternoon flight departure.
USD0, 0h40m

9:00am

Short Visit to Portland Head Light

Quick stop at Maine’s iconic lighthouse in Fort Williams Park, open dawn to dusk.
Free, 1h

10:30am

Airport Check-in and Departure

Allow sufficient time for security checks and boarding processes for your flight.
Varies, Variable
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