Leave Sharon around 7:00 AM for the roughly 6½–7-hour drive to Lubec, following I-95 north through Portland and Bangor, then US-1 toward Ellsworth and the coast. This is a beautiful but remote final stretch, so fill the tank and pick up snacks before leaving Bangor; services become increasingly limited after Ellsworth. Plan a relaxed breakfast or coffee stop around Augusta or Bangor, plus a later fuel break near Ellsworth. Expect the last hour to feel slow and scenic, with winding roads and ocean glimpses rather than fast highway driving. After checking in, park at your lodging and explore on foot where possible—Lubec is compact, and downtown parking is generally easy and free.
After settling in, head to Lubec Brewing Company in the village for a casual late lunch or early dinner. The taproom typically opens in the afternoon, but check its September hours before setting out, since small-town schedules can change after summer. Allow about 1½ hours for locally brewed beer and a relaxed meal; budget approximately $25–45 per person, depending on drinks. From there, drive about 15 minutes to Quoddy Head State Park and West Quoddy Head Light. The park generally closes at sunset, with a small day-use fee—about $4 per Maine resident vehicle and roughly $8 for an out-of-state vehicle, subject to change. Walk the grounds and the short rocky shoreline paths, but bring a light jacket and shoes with good grip: this coast is windy, and the rocks can be slick. Aim to arrive well before sunset rather than counting on the final minutes of daylight.
Return to the village for an easy evening walk along the Lubec Channel waterfront, where you can watch boats move through the narrow passage and look across toward Campobello Island. Allow about 45 minutes, with extra time for photographs as the light fades. The waterfront is quiet after dinner, so this is a good night to keep plans unhurried after the long drive. Temperatures can drop quickly after sunset; carry a warm layer, and check the next morning’s ferry and border information before turning in.
Start early in Lubec and cross the Franklin Delano Roosevelt Memorial Bridge into Campobello Island, bringing passports or other documents accepted for the Canada–US border. The crossing is usually straightforward, but allow 20–30 minutes in case of questions; there is no toll, and cell service can be inconsistent. Arrive at Roosevelt Campobello International Park when it opens—typically around 9:00 AM in September—for the guided tour of the Roosevelt family’s summer home, followed by time in the gardens and carriage roads. Admission is generally free, though donations are welcome; confirm seasonal hours and tour availability before leaving, since early September schedules can change.
Continue a few minutes by car to Herring Cove Provincial Park for a slower late-morning walk along the beach and coastal trails. The park’s day-use fee is modest, and parking is easiest before midday. Pack water and a light lunch or snacks, as facilities on the island are limited and September weather can shift quickly. Afterward, drive toward the southern tip of Campobello Island for East Quoddy Head Lighthouse, viewed from the Campobello shore. Check the tide table before setting out: the lighthouse itself stands on Head Harbour Island, and access depends on tidal conditions, footing, and any local restrictions. Wear sturdy shoes and treat the rocks as slippery even in calm weather.
Return toward Lubec in mid-afternoon, allowing time for the border crossing and a brief pause at the Lost Fishermen’s Memorial on the waterfront. It is a quiet spot to look across the channel toward Eastport and reflect on the area’s fishing history; 30 minutes is plenty. For dinner, book ahead at Water Street Tavern in Lubec village, a dependable local choice for seafood, burgers, and a relaxed harbor-town atmosphere. Expect roughly $30–60 per person with drinks. After dinner, take a short walk along Water Street if the weather is clear, but keep the evening unhurried—tomorrow’s cross-border drive to Saint Andrews is easiest with an early start.
Leave Lubec around 8:30 AM, keeping passports, vehicle registration, and insurance documents handy for the Calais–St. Stephen crossing. The drive via US-1, the International Avenue Bridge, and NB-127 takes about two hours before border formalities. After arriving in Saint Andrews, park near the town center and walk or drive the short distance to Kingsbrae Garden. Plan roughly two hours for its themed gardens, sculpture installations, and quiet paths; September is an especially pleasant time for the late-season displays. Check the garden’s September hours and admission, generally around C$20–30 per adult, before setting out.
Head into historic Saint Andrews for the Ross Memorial Museum, where a one-hour visit is enough to see its regional art, decorative pieces, and local heritage exhibits without rushing. Confirm the seasonal opening schedule—hours can be limited after summer—and expect a modest admission fee or donation. From the museum, continue to the Algonquin Resort grounds and waterfront, an easy stroll through the historic center. Spend about an hour wandering around the resort’s grand exterior, nearby harbor, and water-facing streets; this is a good place to slow down and take photographs rather than add another formal attraction.
For dinner, settle in at The Chandler Room, a polished choice in the historic center with a menu suited to a relaxed evening after driving and sightseeing. Budget approximately C$45–75 per person before drinks and gratuity, and reserve ahead if possible, especially for a Sunday evening in early September. Afterward, take a short walk through downtown Saint Andrews—the waterfront is particularly peaceful around sunset—then return to your accommodation without needing the car.
Leave Saint Andrews around 8:00 AM for Saint John, allowing roughly 1½ hours via NB-127 and Route 1, plus time to park in Uptown. Park once in a public garage or municipal lot near King Square and explore on foot; the compact center is much easier than moving the car between stops. Begin at Saint John City Market, where vendors sell baked goods, produce, prepared foods, and local specialties. It is a good place for breakfast or an early lunch—allow about 1½ hours and roughly C$15–30 per person. Check the market’s current weekday hours before leaving, as individual stalls may open or close on different schedules.
Walk downhill toward the waterfront for the New Brunswick Museum, allowing about two hours for its natural-history, Indigenous, and provincial-history exhibits. The museum’s galleries and opening schedule can change during renovations or seasonal programming, so verify same-day hours and admission—typically around C$10–20 per adult—on the official website. From the Uptown core, the walk is approximately 10–15 minutes, or you can move the car once and use nearby waterfront parking.
After the museum, drive about 10 minutes west to the Reversing Falls Rapids viewpoints in the Fallsview area. Spend 45 minutes watching the Saint John River surge and swirl as the Bay of Fundy tide changes; the effect is most dramatic near the transition between ebb and flood, so check the day’s tide table and treat the viewing platforms as slippery in wet weather. This is a short visit rather than a full attraction, and the viewpoints are generally free, with parking availability varying by overlook.
Return to Uptown for an unhurried evening at Hopscotch Whisky Bar. It is a good place to settle in for cocktails, whisky, and dinner rather than trying to fit in another major sight; budget about C$35–65 per person before tax and tip. Make a reservation if visiting on a Friday or Saturday, and plan to walk or use a short taxi/rideshare trip from your hotel. Expect the bar and kitchen’s hours to vary by season, so confirm the current closing time before heading over.
Leave Saint John around 7:30 AM for Saint Martins, allowing about 1¼ hours on Route 111. Arrive first at Quaco Head Lighthouse, where a short visit—roughly 45 minutes—gives you broad views across the Bay of Fundy and the rugged coastline. The grounds are generally best treated as an outdoor stop, so bring a warm layer and sturdy shoes; wind can make the morning feel considerably cooler than inland Saint John.
Continue into St. Martins for the Sea Caves of St. Martins, timing your arrival strictly around the 2026 low-tide table. The sandstone caves are accessible on foot only while the tide is safely out, and the exact usable window can be shorter than the headline low-tide time. Allow about 1½ hours, wear shoes that can handle wet, uneven ground, and never linger inside a cave as the water begins returning. Check the official tide information and local access conditions before setting out, since beach access and cave exploration can be restricted in rough weather.
After the caves, have a relaxed seafood meal at Spinney’s Seafood near the Saint Martins harbor—plan on approximately C$20–35 per person. Hours can vary in September, so confirm that day’s opening time before relying on it for lunch; if service is limited, take the opportunity for a harbor-side snack and a slower break. Then drive toward Salmon River and spend about three hours on the Fundy Trail Parkway, stopping at the major coastal lookouts and choosing one or two short walks rather than trying to cover every trail. Expect a park admission fee, limited mobile service, and winding roads; download directions beforehand and keep fuel topped up in Saint Martins.
Return to Saint Martins for the evening high tide and spend about 45 minutes along the harbor and shoreline. This is the satisfying contrast to the morning: the cave entrances and rocky beach that were exposed earlier are largely swallowed by the Bay of Fundy, while boats rise dramatically against the wharves. Check the tide table for the precise high-water time and arrive slightly early, then allow extra time afterward if you are driving back to Saint John. The route is dark and rural at night, so avoid rushing and watch carefully for wildlife.
Leave Saint John around 7:30 AM for Alma, following Route 111 through Rothesay and Sussex, then Route 114 toward the coast. The drive takes about two hours, so bring coffee and plan to arrive with plenty of time before low tide. Check the official tide table the evening before, since the exact order and timing at Alma Beach and Hopewell Rocks should follow the day’s tide rather than the clock.
Begin at Alma Beach and harbour, where low tide reveals broad stretches of ocean floor and the fishing boats sit on the seabed until the Bay of Fundy returns. Allow about 1½ hours to stroll along the shoreline, but wear shoes that can handle mud and slippery seaweed, and keep an eye on the water’s return. From Alma, drive roughly 35 minutes to Hopewell Rocks in Hopewell Cape; admission is generally around C$15–25 per adult, with seasonal hours and re-entry rules worth confirming online.
Spend about 2½ hours at Hopewell Rocks, walking among the famous flowerpot formations while the sea is out. The shoreline is reached by a short walk from the visitor facilities, and the exposed rocks are much more dramatic at low tide than from the viewing platforms above. Afterward, allow a little time for lunch or a snack on-site before the afternoon Hopewell Rocks Tidal Exploration. A guided sea-kayaking trip or interpretive program typically lasts about two hours; reserve ahead through the official operator, and understand that kayaking is tide- and weather-dependent. If the water or wind makes kayaking unsafe, the interpretive option is the better backup.
Return toward Alma and stop at the Annapolis Basin Lookout for about 30 minutes. It is a quiet place to stretch your legs and take in the broad coastal scenery before dinner. Finish at Alma Lobster Shop along the harbour for an informal seafood meal—lobster, lobster rolls, and other local catches generally run about C$25–50 per person. Arrive before the evening rush if you want the best selection, and keep the rest of the night easy; after a tide-focused day, the harbour is especially pleasant for a short post-dinner walk.
After breakfast in Alma, drive into Fundy National Park and follow signs toward Dickson Falls Trail. Arrive around 8:30 AM, before the forest trails warm up and before the small parking areas fill. The roughly 1.5-hour walk follows a mossy brook through spruce and fir forest to a pretty waterfall; wooden stairs and damp roots can be slippery, so wear proper hiking shoes. Park admission is generally about C$13 per adult, though fees and passes can change—bring a card and a little cash. Allow extra time if rain has made the trail muddy.
Late in the morning, continue to the Fundy National Park Visitor Centre near the Alma entrance. Spend about 45 minutes checking trail conditions, washrooms, road closures, and the day’s tide information. Rangers can also advise whether the park’s smaller roads and viewpoints are suitable for your car. From there, take the park road toward the Carriage Road Trail; it is a short drive, but allow time for stops at lookouts rather than treating the park like a direct transfer.
Set aside about two hours for the Carriage Road Trail, a quieter woodland route with a more relaxed feel than the signature waterfall walks. Pack a picnic or pick up sandwiches in Alma before entering the park, since food options inside the park are limited and seasonal. Keep an eye on the time: the trail is moderate rather than strenuous, but the combination of roots, rocks, and uneven grades makes it worth carrying water and a light rain layer.
In the afternoon, drive toward Point Wolfe Covered Bridge, one of the park’s most photogenic spots. Plan roughly 45 minutes to walk around the bridge and look down into the wooded river valley; the setting is especially peaceful once tour groups have moved on. The bridge area can be breezy and shaded, so temperatures may feel cooler than in Alma. Return to the village for an unhurried hour along Alma’s harbourfront, where fishing boats sit dramatically low or high depending on the tide. Tide timing varies by date, so check the local tide table at the visitor centre rather than relying on a generic schedule.
For dinner, stay in Alma and choose one of the village’s casual seafood restaurants, ordering local haddock, scallops, lobster, or fish-and-chips when available. Expect approximately C$30–60 per person before drinks and tip; September is quieter than midsummer, but some restaurants reduce hours after Labour Day, so confirm opening times earlier in the afternoon. Finish with a short harbourfront stroll if the light is good, then return to your accommodation—there is little need to drive farther tonight, and the dark rural roads around the park are unlit and wildlife can be active.
Leave Alma around 7:00 AM for the long drive to Portland, allowing seven to eight hours including the border crossing, fuel, and stops. Follow Route 114 toward Moncton, then the Trans-Canada Highway and Route 2 into Maine. Keep passports, vehicle documents, and any food or agricultural items handy for the Canada–US border, and fill the tank before leaving New Brunswick. A practical coffee-and-fuel stop is around Houlton or Lincoln, where services are easier to find than along the more rural stretches.
Around midday, make a brief 20-minute photo stop at Stephen King’s House in Bangor’s West Broadway neighborhood. It is a private residence, so remain on the public sidewalk and avoid blocking driveways; the ornate fence and corner setting make for a quick exterior stop. From there, drive into downtown Bangor and spend about an hour at the Maine Discovery Museum on Main Street. It is a useful indoor break after the highway miles, with hands-on science exhibits and regional displays; check the museum’s September hours before leaving, as weekday schedules can vary. Allow roughly 10 minutes for the drive from West Broadway and use nearby downtown street parking or a public garage.
Continue south on Route 2 and I-295, arriving in Portland in the late afternoon. Check in, leave the car parked, and walk into the Old Port, where the best evening experience is simply wandering the cobblestone streets around Fore Street, Exchange Street, and the waterfront. Give yourselves about 1½ hours to browse small shops, watch the boats around Commercial Street, and settle into the city’s compact restaurant district; from most Old Port hotels, everything is comfortably walkable, though the uneven paving calls for sensible shoes.
For dinner, go to Eventide Oyster Co. on Middle Street for oysters, lobster rolls, and a relaxed seafood meal. Expect approximately $35–65 per person before drinks and tip, and plan for a wait at peak dinner time—arriving around 5:00–5:30 PM is easier than seeking a table after 7:00 PM. Afterward, take an unhurried walk back through the lit-up Old Port rather than moving the car; Portland’s harbor streets are especially pleasant once the daytime traffic has eased.
After breakfast in Portland, drive about 15 minutes south to Fort Williams Park in Cape Elizabeth. Arrive around 8:30 AM, when the parking areas are easiest and the coastal paths are pleasantly quiet. Portland Head Light sits on a dramatic rocky promontory; allow about 1½ hours to see the lighthouse, walk the shoreline, and visit the small museum inside the former keeper’s quarters. Parking is typically around $2–$5, and the park is generally open from sunrise to sunset, though museum hours can vary. Bring a jacket—the headland is often breezier than downtown.
Continue a few minutes south on Shore Road to Two Lights State Park for a short oceanfront walk among the granite ledges and spruce. This is a good final stretch of Maine air before the long drive, with roughly 45 minutes enough for the main viewpoints. The park usually charges a modest day-use or parking fee, and facilities are limited, so use restrooms and pick up coffee or snacks in Cape Elizabeth before leaving.
Head back toward Portland and join I-95 South around noon. The drive to Sharon is roughly 2½ hours in ideal conditions, but on a September Saturday allow three to four hours for traffic around Portsmouth, Newburyport, and the Boston beltway. A convenient lunch or fuel stop is near Portsmouth, or farther south at a service area before reaching the heaviest traffic. Follow I-95 around Boston, then continue via Route 128/I-95 toward Sharon; keep Google Maps or Waze running for live rerouting and expect approximately $15–$25 in fuel and tolls. With a smooth run, you should arrive mid-afternoon; heavier traffic may push arrival into early evening.