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

Morning

Start at Portland Museum of Art when it opens at 10:00 AM—your 8:15 AM start gives you time for coffee and an unhurried stroll through the Arts District first. Allow about 1½ hours inside, especially for the New England galleries and Winslow Homer works. Admission is typically around $25 for adults, with free admission sometimes available through local library programs; check the museum’s schedule before leaving, as hours can vary seasonally. The museum is walkable from downtown, and nearby metered garages are easier than searching for street parking.

Late morning, wander downhill toward Commercial Street through the Old Port, taking roughly 15–20 minutes on foot. This is the best time to see the waterfront while the working harbor is active, and you can browse the brick-lined shops without the heavier afternoon crowds. Continue to Eventide Oyster Co. for lunch; expect about $25–45 per person before drinks, and plan for a wait at peak lunchtime since seating is limited. Their oysters and brown-butter lobster roll are the essentials, though the menu changes with the day’s catch.

Afternoon and Evening

After lunch, walk or take a short rideshare—about 10 minutes—to the Eastern Promenade. Give yourself an hour along the waterfront park and harbor shoreline; it is a welcome change from the busy Old Port, with broad views toward the islands and working piers. From there, continue a few minutes on foot to Fort Allen Park, where benches, open lawns, and harbor overlooks make a quieter finish. Sunset is usually the best light, but bring a light layer: the East End can feel noticeably cooler and windier than downtown. Street parking near both parks is generally free or metered, but arrive earlier if you want an easy space; rideshare back to the Old Port is usually quicker than walking after dark.

Morning

After breakfast, pick up your rental car in Portland and drive about 15 minutes south to Fort Williams Park in Cape Elizabeth. Start with Portland Head Light, then follow the rocky paths around the former fortifications and shoreline; allow roughly two hours. The park is open year-round from sunrise to sunset, with a seasonal parking fee generally around $5–$10 per vehicle. Arrive early for easier parking and calmer views—the lighthouse grounds get busy later in the morning.

Continue about 10 minutes south to Two Lights State Park, where short coastal trails lead to broad ocean views and wave-battered granite. Spend about an hour here, keeping an eye on the uneven footing near the cliffs. For lunch, walk or drive a few minutes to The Lobster Shack at Two Lights, an unfussy seasonal spot perched above the water. Order at the counter and expect roughly $25–45 per person; hours are seasonal, so check the same-day schedule before setting out, and bring a layer because the deck can be breezy even in September.

Afternoon and Evening

From Cape Elizabeth, drive approximately 35–45 minutes via local roads and US-1/SR-9 to Kennebunkport’s Dock Square. Park in a public lot rather than trying to find curb space in the center, then spend an easy hour and a half browsing galleries, small boutiques, and the Kennebunk River waterfront. This is a good place to slow down—walk across the bridge, look for a café or ice cream stop, and enjoy the village atmosphere rather than packing in another formal attraction.

Late afternoon, drive about 10 minutes to Goose Rocks Beach for a broad sandy walk and a quieter end to the sightseeing day. Check the posted parking rules carefully; beach parking is often restricted or permit-controlled, and September access can change by time of day. Afterward, return to Kennebunkport for dinner, roughly 15–20 minutes away, and keep the evening relaxed—many restaurants fill early, so reserve ahead if you want a waterfront table.

Morning

Leave Kennebunkport after breakfast—around 7:45–8:00 AM—to reach Rachel Carson National Wildlife Refuge in Wells before the coastal roads become busy. The drive is roughly 35–40 minutes via US-1 and Maine Route 9. Park at the Carson Trail lot and allow about an hour for the easy loop through salt marsh, spruce woods, and tidal inlets; bring bug spray and binoculars, and stay on the marked trail to protect nesting habitat. From there, it’s about 15 minutes north to Ogunquit, where you can park in town or near Perkins Cove—expect paid parking, commonly around $20–30 for the day in summer. Walk the Ogunquit Marginal Way north toward the cove, allowing 1½ hours for the rocky overlooks and benches; it’s an easy path, but wear shoes with decent grip.

Lunch and Afternoon

Finish at Perkins Cove and have lunch at Barnacle Billy’s, a longtime local favorite for lobster, steamers, and fried seafood at picnic tables overlooking the harbor. Budget roughly $30–55 per person, and expect a line at midday; counter service keeps things moving, but it’s smart to arrive before 12:30 PM. After lunch, set the GPS for Marshall Point Lighthouse in Port Clyde—about 1 hour 45 minutes via US-1 and Maine Route 131, with the final stretch narrowing into a quiet peninsula road. The lighthouse grounds are generally open during daylight, while the small museum’s hours can vary; allow an hour to walk the granite shoreline and see the distinctive white keeper’s house and breakwater. This is a good place to slow down rather than rush—the exposed rocks and open water are the real attraction.

Evening

Continue about 45 minutes to Camden, arriving around 5:30–6:00 PM. Leave the car at your lodging or use village parking, then walk to Camden Harbor Park and Amphitheatre, where the lawns rise above the harbor and schooners often return in the late afternoon. Spend an hour watching the boats and exploring the compact village afterward; Bay View Street and Chestnut Street are especially pleasant for an unhurried stroll. For dinner, choose a restaurant in downtown Camden rather than driving again—reservations are worthwhile on a September weekend, and the harbor-facing tables fill first.

Morning

Begin at Mount Battie in Camden Hills State Park, ideally around 8:00 AM. The summit road is usually open seasonally from roughly 9:00 AM, so before then the best option is the moderate 1.5-mile Mount Battie Trail from the Camden Hills State Park parking area; if the auto road is open, driving up is an easy alternative. Allow about 1½ hours for the summit, stone tower, and views over Camden Harbor and Penobscot Bay. The park generally charges a modest day-use fee, and the summit can be windy even in September—bring a light layer. Afterward, follow US-1 north for about 15 minutes to Cellardoor Winery at Thompson’s Point in Lincolnville.

At Cellardoor Winery, settle in for a relaxed late-morning tasting among the gardens and fields rather than rushing through a flight. Tastings typically cost about $15–30 per person, and the tasting room commonly opens around 11:00 AM, though reservations are wise on weekends. Plan on roughly 1½ hours, with a small snack if needed; designate a driver and remember that Maine’s tasting-room hours can change seasonally. From here, the drive to Blue Hill takes about 50–60 minutes via US-1 and ME-172.

Afternoon and Evening

Arrive in Blue Hill in the mid- to late afternoon and spend an hour wandering the compact village before heading down toward Blue Hill Harbor. Browse the independent shops around Main Street, then continue toward the waterfront for a quiet look at the tidal flats and working-harbor scenery. It is a good place to slow down—there are no major attractions to queue for, and low tide can make the harbor feel especially expansive. Keep dinner timing in mind: The Lost Kitchen in Freedom is roughly an hour away, and its reservation-only dinners are famously difficult to secure. If you do have a reservation, leave Blue Hill with generous time for the rural drive and arrive early; expect a long seasonal tasting-style meal costing approximately $75–150 per person. If not, stay local and choose a farm-to-table dinner in or near Blue Hill rather than making the unnecessary drive.

Finish with Blue Hill Mountain, whose trailhead is only a short drive from the village. Allow about 1½ hours for the climb and descent, choosing the timing so you reach the summit before sunset; the open ledges provide broad views across the peninsula and surrounding islands. Bring a headlamp for the walk back if dusk comes quickly, and check the forecast before setting out—wet rock can be slippery. Since Blue Hill is quiet after dark, this is a good night to keep plans simple and turn in early for the next morning’s drive toward Acadia National Park.

Morning

Leave Blue Hill around 6:30–7:00 AM for Jordan Pond in Acadia National Park—the drive to the park is roughly 1¼–1½ hours via ME-172, US-1, and ME-3. Arriving early is worthwhile: the Jordan Pond lot fills quickly, and the shoreline is at its quietest before the tour buses and midday crowds. Walk the Jordan Pond Path for a close look at the Bubbles reflected in the water; the full loop is about 3½ miles and takes roughly two hours, though you can turn back sooner if the boardwalk sections are damp or busy. Carry water and a light layer, since the lakeshore can feel cool even on a sunny September morning.

After the walk, settle in at Jordan Pond House for its famous tea and popovers, ideally late morning before the main lunch rush. Budget about $15–35 per person, and expect a short wait on a pleasant day; the lawn and classic view toward the Bubbles are as much of the experience as the food. From here, drive to Cadillac Mountain—allow about 30 minutes, including the park roads and parking. A timed vehicle reservation is required during the reservation season, separate from the park entrance pass, so confirm the available window on Recreation.gov before leaving. Give yourself about 1½ hours at the summit for the panoramic views across Frenchman Bay and the Porcupine Islands; September weather can change quickly, so bring a jacket.

Afternoon and Evening

Continue down the Park Loop Road to Sand Beach, roughly 20 minutes from Cadillac Mountain. Spend about 45 minutes walking the shoreline and the nearby rocky edges, but don’t plan on a long swim—the water is cold even in summer. Parking is tight, so if the lot is full, use the Island Explorer shuttle when operating or circle back after a quieter period rather than stopping on the road shoulder. Then make your way to Bar Harbor, usually a 20–30-minute drive depending on traffic, and check in or leave the car at your lodging; downtown is easiest on foot.

At low tide, stroll the Bar Harbor Shore Path for about an hour, starting near the village waterfront and following the harbor past the old hotels and working docks. Check the tide table first and stay well clear of the exposed sandbars, where the incoming tide can cut off routes surprisingly fast. Finish at Side Street Cafe, a relaxed village spot for burgers, seafood, and local beer; allow roughly $20–40 per person. It is popular in the evening, so arriving before the dinner rush or adding your name to the waitlist early will make the night much easier.

Morning

Leave Bar Harbor around 8:00 AM on ME-3, joining US-1 and then I-295 south. The full drive to Portland is about 3–3½ hours without stops, but build in extra time for the two planned detours. Your first stop is the Penobscot Narrows Bridge and Observatory near Bucksport, roughly 1½ hours from Bar Harbor. The observatory rises inside the bridge tower and offers a remarkable view up and down the Penobscot River; allow about an hour, and check the seasonal opening schedule before setting out, as hours can vary in September. There is convenient parking at the bridge grounds, and the modest admission fee is generally under $10.

Afternoon

Continue south toward Bath, where the Maine Maritime Museum makes an excellent early-afternoon stop. Set aside around two hours for the waterfront campus, historic vessels, shipbuilding exhibits, and the former Percy & Small Shipyard—this is a particularly good rainy-day option, but the outdoor exhibits are enjoyable in fair weather too. Museum hours are commonly around 9:30 AM–5:00 PM in season; admission is typically about $20–25 for adults. From Bath, allow roughly 45 minutes to reach Portland, depending on traffic, and return the rental car if your lodging is walkable from downtown; otherwise, confirm whether your hotel has parking before entering the peninsula, where evening spaces can be tight.

Evening

Celebrate the final drive at Solo Italiano in Portland’s East End, a short taxi or rideshare trip from downtown. The handmade pastas and northern Italian-leaning menu are ideal for a relaxed farewell dinner—expect roughly $30–60 per person before drinks, and reserve ahead if possible. Afterward, take an easy stroll along nearby Washington Avenue rather than trying to fit in another attraction; the neighborhood’s converted warehouses, small bars, and harbor air provide a fittingly unhurried end to the trip.