Leave Sharon around 6:30 AM for the roughly 7–8-hour drive to Saint Andrews, using I-95 North through New Hampshire and Maine before continuing on Route 1 toward the border. Build in time for fuel, coffee, and a proper lunch stop rather than trying to make the drive nonstop. Keep passports readily accessible: you’ll cross from the United States into Canada at St. Stephen, and border delays can vary. Check current CBP/CBSA wait times before departure, and remember that the clocks remain on Eastern Time.
After arriving in Saint Andrews, park at your lodging and take a short walk along Water Street, the town’s easygoing waterfront strip. Allow about an hour for harbor views, small galleries, historic buildings, and glimpses across Passamaquoddy Bay. Parking is generally straightforward along nearby streets, but leave the car behind once you arrive—the compact center is pleasant on foot.
Continue uphill to Kingsbrae Garden, allowing about two hours before closing; in early September, verify the day’s hours online, as seasonal closing times can be around 5–6 PM. The landscaped gardens, woodland paths, and coastal viewpoints are a welcome change after the long drive. Wear comfortable shoes and leave enough time to enjoy the quieter outer trails rather than rushing through every garden section.
Early evening, stop at The Algonquin Resort for about 30 minutes to admire its grand historic exterior and grounds. Then walk or drive a few minutes into the center for dinner at The Shiretown Public House. Expect roughly C$30–50 per person for pub fare and drinks; reservations are sensible on a Friday night. After dinner, take a brief waterfront stroll if you still have energy, but keep the evening relaxed—tomorrow’s Campobello Island outing involves an international border crossing and an early start.
Leave Saint Andrews around 7:30–8:00 AM for Roosevelt Campobello International Park, allowing about an hour via Route 127 and the International Avenue Bridge. Bring passports: the drive briefly crosses through Maine before re-entering Canada. After the Canadian checkpoint, continue to the park and begin with the visitor exhibits and coastal trails; parking is straightforward at the main sites, but bring water and layers because the island can be notably windy. Park access is generally seasonal and hours vary, so confirm the 2026 schedule and any entrance fees before leaving.
Late morning, tour Roosevelt Cottage, the former summer retreat of Franklin and Eleanor Roosevelt. Allow about an hour for the house and interpretation, then take your time walking among the spruce woods and open shoreline around Roosevelt Campobello International Park rather than trying to see every trail. The cottage and park facilities typically operate daytime hours in September, but guided-tour times can be limited after Labor Day—arrive early enough to join the next available tour.
Drive south toward Herring Cove Provincial Park, roughly 15–20 minutes depending on your starting point, for an easy beach walk and broad views across the bay. Allow about 1½ hours; the beach is ideal for a quiet picnic, though services become more limited after summer, so carry snacks and water. Continue north to Head Harbour Lighthouse for the late-afternoon visit. Check the tide and access conditions before setting out: reaching the lighthouse can involve walking across exposed ocean floor, and the route should never be attempted as the water begins returning. Give yourself plenty of time to turn around, and use sturdy footwear rather than sandals.
Finish at The Gables Restaurant in Welshpool, a convenient 15–20-minute drive from the lighthouse. Reserve ahead if possible, since September dining options on the island are limited and hours may be reduced after the summer rush; budget approximately C$35–60 per person before drinks and gratuity. It is worth confirming that the restaurant is open on your chosen evening, then return to your accommodation without rushing—the island roads are dark and wildlife is common after sunset.
Since you are already on Campobello Island, cross back into Maine via the International Avenue Bridge and allow roughly 35–45 minutes to reach West Quoddy Head Light in Lubec, depending on the border crossing. Bring passports and leave around 8:00 AM; the lighthouse grounds are generally accessible from sunrise, though the tower’s interior hours are seasonal. Parking is straightforward, and the short Quoddy Head State Park trails lead to dramatic ocean overlooks—bring a windproof layer, even in September.
Continue into Lubec Channel Historic District for an easy waterfront walk along Water Street and Main Street, where old commercial buildings face the channel and Campobello Island sits just across the water. This is a good place for coffee or a light snack, but expect limited Sunday-morning service in this small coastal town. Walk rather than drive between the waterfront viewpoints, and keep an eye on the tide and fishing activity around the harbor.
Next, visit McCurdy Smokehouse Museum, a compact but atmospheric look at Lubec’s herring-smoking history. Set aside about 45 minutes; hours can be limited and volunteer-run, so verify the 2026 opening schedule before setting out. Afterward, drive back across the bridge into Canada and continue toward Friars Bay Development Centre in Welshpool. Allow about 30–40 minutes including the border crossing. The beach is peaceful and uncrowded, with good opportunities for shorebirds and a quiet walk; check the tide before visiting, since the shoreline character changes considerably through the day. Bring binoculars, water, and footwear suitable for damp sand.
Finish at Friars Bay Inn & Cottages, a short drive from the beach, for dinner. Plan on approximately C$30–50 per person, but call ahead to confirm that the restaurant is serving on this Sunday in September and ask about kitchen hours. It is a relaxed place to end the day rather than a quick stop, so allow about 90 minutes. If you are staying elsewhere on Campobello Island, return after dinner while daylight remains if possible; the roads are quiet but rural, and wildlife can appear near the verges.
Leave Campobello Island around 8:30 AM for St. Martins, following Route 127 toward Saint John and then Route 111; allow roughly 3½–4 hours including stops. The practical plan is to make Saint John City Market your fuel-and-lunch break. It is a compact, historic indoor market where you can browse local produce, baked goods, seafood, and prepared foods in about an hour. Check the market’s September weekday hours before leaving, as individual vendors keep their own schedules; budget approximately C$15–25 per person for lunch and snacks. Parking is available in nearby garages and paid lots, and it is easier to leave the car parked while you walk through the market than to move it between stops.
After lunch, drive about 10 minutes to Reversing Falls Rapids for a 30–45-minute look at the powerful tidal currents where the Saint John River meets the Bay of Fundy. The rapids change character with the tide, so do not expect the most dramatic appearance at every visit; check the day’s tide table and use the signed viewpoint or nearby public lookout rather than stopping along the roadway. From Saint John, continue east on Route 111 toward St. Martins, arriving in the late afternoon. At St. Martins Sea Caves, plan about 1½ hours and aim for the lower-tide window listed in the official access information—parts of the beach can be inaccessible or unsafe when water is rising. Wear shoes that can get wet, bring a light jacket, and confirm parking, cave access, and any shuttle or admission requirements before setting out.
Finish at Sea Caves Restaurant, conveniently close to the caves, for dinner—reserve if reservations are accepted, since September evenings can still be busy with visitors timing their meal around the tide. Expect roughly C$30–50 per person before drinks and tip. Order something local if available, but keep the evening relaxed: the coast is especially pleasant after dinner, when the crowds thin and the cliffs and shoreline take on a softer light. Keep the drive back to your St. Martins accommodation short, and check the next day’s tide times before turning in.
Start around 8:00 AM from St. Martins, heading east along the coast toward the entrance of Fundy Trail Parkway. Allow roughly 20 minutes to reach the gate, and plan on spending most of the day inside; admission is generally about C$13–15 per adult, with possible changes for the 2026 season. The parkway is a slow, scenic drive rather than a shortcut, so fill the tank first and bring water, snacks, and a light jacket. Stop at the main lookouts and choose only a few short trails—weather can shift quickly on the exposed cliffs, and the road’s full length takes longer than the map suggests.
Make Long Beach your late-morning stop, allowing about 45 minutes to take in the wide shoreline and forested headlands. Do not assume the beach will look the same as it does in photographs: the Bay of Fundy’s enormous tidal range can cover much of the sand, and slippery rocks or mud may be exposed at lower water. Continue along the parkway to Walton Glen Gorge Lookout around midday. Give yourselves about 30 minutes here for the dramatic gorge view, then use one of the designated picnic areas for lunch or eat the provisions you brought; food choices inside the parkway are limited and seasonal.
After the gorge, continue exploring the remaining viewpoints at an unhurried pace, then return toward St. Martins in the mid-to-late afternoon. Allow at least 45 minutes for the drive back, plus extra time for photo stops. At St. Martins Harbour, spend about an hour walking the wharves and watching the tide work around the fishing boats and shoreline. This is a particularly good place to compare the water level with what you saw earlier along the parkway, but stay off closed sections and keep well back from the rocks—the Bay can rise quickly.
For dinner, walk or drive to Britt’s Pub & Eatery, where a casual meal generally runs about C$25–45 per person before drinks and tax. September hours can vary, so check the same-day schedule and kitchen closing time before leaving the harbour. After dinner, take a short waterfront walk if the light is good; otherwise, call it an early night, since tomorrow’s transfer toward Hopewell Cape is more enjoyable with an early start.
Leave St. Martins around 8:00 AM via Routes 111 and 114, allowing roughly 2½ hours with a fuel or coffee stop. Check the official Hopewell Rocks tide table before setting out—the shoreline is only safely accessible during the designated low-tide window, and the exact timing varies daily. Park at the main visitor site, wear shoes that can handle wet mud and uneven rock, and allow about 2½ hours to walk among the Flowerpot Rocks. The shuttle is useful if you want to save energy or return to the elevated viewpoints after exploring the ocean floor; admission and shuttle arrangements are best confirmed online before leaving.
After the walk, spend about 45 minutes at the Hopewell Rocks Tidal Exploration Site, where the interpretive displays explain the Bay of Fundy’s extraordinary tidal range and include important guidance about rising water and slippery surfaces. Don’t linger below the cliffs once staff advise visitors to return—the tide comes in surprisingly quickly. A short drive west brings you to Cape Enrage, where you can spend roughly 1½ hours taking in the lighthouse, rugged cliffs, and wide views over the bay; seasonal ziplining or rappelling may be available, but check operating hours and weather conditions in advance.
From Cape Enrage, continue to Chocolate River Station in Hillsborough for dinner, allowing time for the drive and a relaxed meal of about 1½ hours. Budget approximately C$25–45 per person. This is a good place to wind down rather than add another attraction: the day’s combination of an exposed tidal shoreline, interpretive exhibits, and cliff scenery is plenty. Keep a light jacket in the car—even on a warm September afternoon, the Fundy coast can turn cool and windy once you leave the sheltered roads.
From Hopewell Cape, drive west on Route 114 toward Fundy National Park and Alma, allowing about 45 minutes to the park area and roughly another 20 minutes to the village. Enter through the Point Wolfe or Alma side depending on your chosen trail and the day’s weather; September mornings can be cool, foggy, and wet, so bring waterproof layers and sturdy shoes. Spend about three hours on a scenic coastal drive with one moderate walk selected at the visitor centre or from Parks Canada’s current trail conditions. Park Canada admission is generally around C$11 per adult, though rates and passes can change; carry water, as services are limited once you leave Alma.
Continue to Alma Harbour, a short drive from the park entrance, for an easygoing lunch among fishing boats, tidal flats, and working wharves. Alma Lobster Shop is a practical choice for straightforward seafood, while Buddha Bear Coffee Roasters is useful for coffee or something light afterward; allow about an hour and check seasonal September hours before setting out. Time your harbour walk around the tide—the mudflats change dramatically, and the fishing boats may appear to sit on the bottom at low water. After lunch, drive roughly 30 minutes to Cape Enrage Lighthouse near Waterside. Allow an hour for the lighthouse, cliff-top views, and the shoreline below; admission is typically around C$6–10 per adult, and the access road is rural, so do not leave this stop too late.
From Cape Enrage, drive about 45–55 minutes to the Moncton waterfront, aiming to arrive well before the Petitcodiac River tidal bore. Check the official tide table on the day—viewing times are approximate, and the incoming wave can be subtle, particularly after wind or unusual river conditions. The best low-effort viewing is from the Riverfront Park boardwalk near downtown; parking is usually available nearby, and allow 30 minutes, with extra time to watch the river surface change. For dinner, walk or make a short drive to Little Louis’ Oyster Bar, where reservations are sensible on a Friday or Saturday and a seafood-focused meal will generally run about C$35–60 per person before drinks and gratuity. Expect a relaxed finish rather than a quick meal, then return to your Moncton accommodation; downtown parking is generally easiest before the dinner crowd arrives.
Leave Moncton around 7:00 AM for the drive to Portland, using the Trans-Canada Highway 2, Route 2, and I-95. Allow 6½–7½ hours with fuel, meal, and border stops; keep passports readily accessible and check both CBSA and U.S. Customs and Border Protection wait times before leaving. A useful break is around Bangor, where you can refuel and stretch before continuing south. On arrival, go directly to Cape Elizabeth rather than trying to park in downtown first; after a long drive, the open shoreline at Portland Head Light is an easy way to reset. Parking is generally available in the park lot, though it can fill on pleasant afternoons, and the grounds are free to visit. Give yourselves about an hour for the lighthouse, coastal paths, and rocky viewpoints.
Drive back toward the city and spend roughly 45 minutes at the Eastern Promenade, one of Portland’s best low-effort sunset stops. The waterfront park has broad views across Casco Bay, benches, and room to wander without the crowds of the Old Port. Use the public lots near Eastern Promenade Road or nearby residential streets where permitted; parking rules are enforced, so read signs carefully. From here, it is about a 10-minute drive—or a pleasant longer walk if you still have energy—into the center of town.
Finish in the Old Port, wandering the cobbled lanes around Middle Street, Fore Street, and the waterfront for about an hour. Most shops close around 6:00–7:00 PM, but the neighborhood is liveliest in the evening, with working wharves, brick warehouses, and plenty of bars and galleries still open. Have dinner at Eventide Oyster Co. on Middle Street; expect approximately US$35–65 per person before drinks and tip. It is popular and seating can be limited, so check the current queue or reserve if available. Leave the car parked and explore on foot—the compact streets are much easier than trying to move between spots, and garage parking is often the least stressful option for the evening.
Leave Portland around 8:00 AM via I-95 South; the drive to Kittery takes roughly an hour in light traffic. Start with about 90 minutes at Kittery Premium Outlets, where the open-air layout is easiest before the parking lots and stores get busy. Most shops generally open around 10:00 AM, so if you arrive earlier, use the time for coffee and a quick stretch rather than waiting at the doors. Keep purchases accessible in the car and avoid leaving valuables visible.
Continue to Market Basket in Portsmouth for an inexpensive late-morning lunch and road supplies—allow about 30 minutes. It is a practical stop for sandwiches, fruit, drinks, and anything you do not want to buy at highway prices. From there, return toward Kittery and follow local roads to Fort McClary State Historic Site; the fort and shoreline make a worthwhile final pause after several long driving days. Allow about an hour for the historic earthworks, harbor views, and coastal walk. Check the current seasonal hours and parking fee before going; the grounds can close earlier than expected outside midsummer.
Leave Fort McClary by roughly 2:00 PM and rejoin I-95 South toward Sharon, allowing about 1½ hours in clear traffic, plus extra time for the Boston-area approach. A final fuel stop in southern New Hampshire or near Peabody is sensible before the busiest stretch. Traffic can build quickly around Boston, especially on a Friday afternoon, so use live navigation and be prepared for a slower final leg; you should reach Sharon by midafternoon to early evening depending on congestion.