6-Day Roundtrip Road Trip from Portland to Bar Harbor, Maine

Late Morning: Portland Head Light and Fort Williams Park

If you have a car, head to Portland Head Light in Cape Elizabeth around 10:30 AM; it’s roughly a 15-minute drive from downtown Portland. The lighthouse grounds are open from sunrise to sunset, though the museum and keeper’s quarters generally keep more limited daytime hours. Allow about an hour for the lighthouse, rocky viewpoints, and photos, then continue directly into Fort Williams Park for another hour of easy coastal walking among the old batteries, grassy lawns, and shoreline paths. Parking is usually available in the park, but September can still be busy; expect a seasonal parking fee of roughly $5–10, and wear shoes with good grip near the rocks.

Lunch: Eventide Oyster Co.

Return to the Old Port for lunch at Eventide Oyster Co., about 15–20 minutes from the park depending on traffic. Their compact dining room is popular, so arriving around 12:30 PM is sensible; expect a wait at peak lunch time, with limited seating and a lively, casual atmosphere. Order a selection of oysters and the Maine-style lobster roll—budget approximately $25–45 per person before drinks and tip. The restaurant is on Middle Street, and nearby public garages are usually easier than searching for street parking in the historic district.

Afternoon and Late Day: Portland Museum of Art and Eastern Promenade

After lunch, walk or drive a few minutes to the Portland Museum of Art on Congress Street. Plan about 1½ hours for its modern and American collections, with admission typically around $25 for adults; check the museum’s current Tuesday hours before setting out, as schedules and exhibitions can change. From there, finish in the East End at the Eastern Promenade, a short drive or roughly 20-minute walk uphill from downtown. Follow the waterfront path toward East End Beach for broad views across Casco Bay, then linger on the grassy promenade as the light softens. Sunset is a particularly good time here, and there’s no admission charge; if you’re tired, use a rideshare rather than dealing with evening parking downtown.

Morning in Kennebunkport

Start in Kennebunkport around 8:45 AM, when Dock Square is still pleasantly quiet. Allow about 90 minutes to browse the small galleries, clothing shops, and coastal boutiques along Dock Square and Western Avenue. Most businesses open around 9:00 or 10:00 AM, and street parking is limited, so use a public lot near the village center rather than circling. The walk is compact and easy, with plenty of time to pause along the Kennebunk River.

Around 11:30 AM, drive roughly 10 minutes to The Clam Shack in neighboring Kennebunk, perched above the Kennebunk River bridge. This is the place for a classic Maine fried-clam roll, though lobster rolls, fish sandwiches, and fries are also dependable choices; expect about $15–30 per person. It is casual, seasonal, and often busy at lunch, so order before noon if you want to avoid the longest line. After eating, allow another 10 minutes by car to reach the public viewing area for Walker’s Point. The overlook gives you a respectful, distant view of the Bush family’s coastal compound—there is no public access beyond the viewpoint—so 30 minutes is plenty.

Afternoon and Evening in Boothbay

Continue north toward Coastal Maine Botanical Gardens, arriving around 2:00–2:30 PM. Plan on approximately 2½ hours here; the grounds are extensive, with woodland paths, ornamental gardens, sculptures, and seasonal displays that reward an unhurried walk. September is a particularly good time for the late-summer color, but check the gardens’ current closing time and admission online before leaving, since hours and ticket prices vary seasonally. From the gardens, allow about 15 minutes to drive into Boothbay Harbor, where you can finish the day with a relaxed stroll along the waterfront, across the footbridge, and past the working-boat docks. The harbor is best enjoyed without a strict agenda; choose a waterside spot for dinner, and remember that many kitchens stop seating earlier than you might expect after Labor Day.

Morning: Marshall Point Lighthouse & Museum

Leave Boothbay Harbor around 8:00 AM and follow US-1 north, then the scenic roads toward Port Clyde; allow roughly 1 hour 20 minutes of driving, plus a little extra for the final winding approach. Start at Marshall Point Lighthouse & Museum, where a short path leads from the small museum to the white lighthouse and its distinctive walkway over the granite shoreline. Give yourself about an hour to explore the rocks and watch the fishing boats offshore. The grounds are generally open during daylight, while museum hours are seasonal and can vary, so check the posted schedule before relying on an interior visit. Parking is free, but space is limited on busy mornings.

Late Morning and Afternoon: Rockland Breakwater Lighthouse and Farnsworth Art Museum

Continue to Rockland—about 25 minutes from Port Clyde—and park near the Rockland Breakwater Lighthouse entrance. The nearly mile-long granite breakwater is an easy, level walk but exposed to wind and spray; wear shoes with good grip and allow about 1½ hours round trip. There are no facilities at the lighthouse, so bring water and use restrooms in town beforehand. Back downtown, walk or drive a few minutes to the Farnsworth Art Museum for an hour and a half with Maine-focused art, including the Wyeth family collection. It is typically open Tuesday through Saturday from late morning into the afternoon; admission is usually around $20–25 for adults, with reduced rates for seniors and students. Rockland is compact enough to explore on foot once parked, though a car is useful for the breakwater.

Evening: Dinner and Harbor Walk

Have dinner at 2 Cats Restaurant, a relaxed downtown spot known for creative, locally sourced cooking; budget approximately $25–50 per person, and reserve ahead if possible because the dining room is small. Afterward, take a gentle 45-minute stroll along Rockland Harbor, following the waterfront parks and harborfront paths as the boats settle into the evening. Sunset light over the working harbor is especially good from the public waterfront, and this is a pleasant time to slow down rather than add another formal stop.

Morning: Schoodic Peninsula

Leave Rockland around 8:00 AM and make Schoodic Peninsula your main scenic stop before continuing to Bar Harbor. Allow about 2½ hours here, plus driving time: the coastal loop is quieter than the park’s busiest roads and gives you broad views of granite ledges, spruce forest, and the open Atlantic. Stop at Schoodic Point for the classic wave-battered shoreline, then take one or two short walks near Raven’s Nest or Frazer Point rather than trying to fit in a longer hike. Pack coffee and something small to eat, since services on the peninsula are limited; the park itself has no entrance booths here, but an Acadia pass is still required and costs about $35 per private vehicle for seven days. Continue toward Bar Harbor in the early afternoon, allowing roughly 1½–2 hours after leaving Schoodic, depending on traffic and photo stops.

Afternoon: Bar Harbor Shore Path and Abbe Museum

After checking in or leaving the car at your lodging, walk into downtown Bar Harbor and follow the Bar Harbor Shore Path for an easy waterfront hour. It begins near the town pier and is best enjoyed slowly, with views toward the Porcupine Islands and the mountains across the bay; avoid moving your car again, as central parking is limited and often metered. From the path, it is only a short walk through downtown to the Abbe Museum, generally open in September from late morning into the afternoon; allow about an hour for its thoughtful collection of Wabanaki art, history, and contemporary culture. Admission is typically around $10–15 for adults, with schedules and prices worth checking before you arrive.

Evening: Dinner and sunset at Agamont Park

For a relaxed dinner, head to Side Street Café, a casual downtown favorite known for seafood, burgers, and generous comfort-food portions; expect roughly $20–40 per person before drinks and arrive early or be prepared for a wait, since September evenings can still be busy. Afterward, walk a few minutes to Agamont Park rather than driving. The waterfront lawn is an easy place to watch boats return and the light fade over the harbor—sunset is around 7:00 PM in early September—so bring a light layer, especially if the breeze comes up.

Early Morning: Cadillac Mountain

Start before sunrise from Bar Harbor and drive into Acadia National Park for your timed vehicle reservation at Cadillac Mountain. In early September, sunrise is roughly 5:55–6:00 AM, so aim to arrive 20–30 minutes before your reserved window; the drive from downtown takes about 25 minutes, and parking fills quickly even with a reservation. The summit road is open seasonally, but access requires both the park entrance pass—about $35 per private vehicle, valid for seven days—and a separate Cadillac Summit Road reservation, typically around $6. Bring layers and a flashlight: the summit is noticeably colder and windier than town. Give yourself about 90 minutes for the overlook, short summit paths, and changing light over Frenchman Bay.

Late Morning to Midday: Sand Beach and Ocean Path

Drive down the one-way Park Loop Road toward Sand Beach, allowing time for the scenic pullouts and possible traffic. Spend about 45 minutes on the sand and surrounding rocks; swimming is possible but the water is very cold. From here, walk the Ocean Path south toward Thunder Hole, a dramatic shoreline route of about 1.5 miles each way if completed to the main viewpoint. The trail is mostly easy but rocky in sections, so wear shoes with good grip and carry water. Thunder Hole is most impressive around two hours before high tide, although the surf is never guaranteed to “boom”; check the day’s tide table before setting out. Return to the Sand Beach area or continue by car along the loop, depending on your energy and parking conditions.

Afternoon and Late Afternoon: Jordan Pond House and Jordan Pond Shore Path

Continue along the park roads to Jordan Pond House for a relaxed lunch beside the water, usually open seasonally from late morning through the afternoon. Expect roughly $25–50 per person, and try the famous popovers with jam if they are available; a wait is common, so joining the list on arrival is sensible. After lunch, take the Jordan Pond Shore Path from near the restaurant. The full loop is about 3.5 miles and can take 1.5–2 hours because of roots, rocks, and boardwalk sections, but an out-and-back along the quieter shore is a good choice if you are tiring. Parking at the pond is limited and often fills by midday; if the lot is full, use the Island Explorer shuttle where operating rather than circling, and return to Bar Harbor after the walk for an easy dinner and harbor-front wandering.

Morning: Bar Harbor to the Penobscot Narrows

Leave Bar Harbor around 8:00 AM after refueling, following ME-3 and US-1 toward Bucksport. The direct drive is roughly 1½ hours, but allow extra time for the winding roads and a coffee stop if needed. Your first break is Penobscot Narrows Bridge & Observatory, where the observation tower offers sweeping views over the Penobscot River and surrounding forests. The observatory is generally open seasonally from late morning into the afternoon; admission is usually about $7–$10, and the adjacent parking is straightforward. Allow around an hour, and check the day’s opening time before setting out, as hours can vary in September.

Early Afternoon: Belfast Harborwalk

Continue south on US-1 for about 35 minutes to Belfast, a good place to pause before the final leg to Portland. Follow the waterfront to Belfast Harborwalk, an easy stroll beside the working harbor with benches, boat views, and access to downtown galleries and shops. Give yourself about an hour here; the walk is free, and downtown cafés provide an easy takeaway lunch if you did not pack one. Belfast is compact, so park once near the waterfront and explore on foot rather than moving the car.

Mid-Afternoon: Freeport and the Drive to Portland

From Belfast, allow roughly 1 hour 15 minutes to reach Freeport via US-1 and I-295. Stop at the Thos. Moser Showroom for about 45 minutes to see beautifully made hardwood furniture crafted in Maine; it is more of a design and craftsmanship visit than a conventional souvenir stop, and admission is free. Check the showroom’s current weekday hours before going, as they can change seasonally. Depart around 3:30 PM for the approximately 30–40-minute drive into Portland via I-295, allowing extra time for afternoon traffic; return the rental car or settle into your Portland lodging by late afternoon.