Cornelius Amann
October 06, 2026
5/5
New England Fall Colours and Acadia for three generations
6 days from Boston for three generations: the Mount Washington Cog Railway, Bar Harbor and Acadia National Park, and Portland.
6 days · Round trip from Boston · up to 12 guests
The Mount Washington Cog Railway in late September Photo: Tony Hisgett from Birmingham, UK, CC BY 2.0, via Wikimedia Commons (https://commons.wikimedia.org/wiki/File:The_Start_of_Mount_Washington_Cog_Railway_2_(6234747837).jpg)
The facts
At a glance
- Length
- 6 days, 5 nights
- Start and end
- Round trip from Boston
- Group size
- 7 to 12 guests
- Longest drive
- 5 h on day 3
- Activity level
Easy
Walks of 1 to 3 km a day on level paths, boardwalks and town streets, never far from the van. The Cog Railway and the Mount Battie road do the climbing; the only rough ground is the granite of the Ocean Path and the Mount Washington summit, and both can be skipped. Up to about 3 hours a day in the van on four days, in legs of about 2 hours or less. Two days are longer: about 5 hours on day 3, when we cross Maine in three legs broken by Freeport and lunch in Camden, and about 4 hours on day 5, Acadia in the morning and then Portland with a break halfway.
- Meals included
- 5 breakfasts, 4 lunches, 2 dinners
- Room of your own
- + CAD 855 (estimated price)
- Season
- Late September to mid-October
Highlights
Why this trip
- The Mount Washington Cog Railway to the summit of the Northeast's highest peak, running since 1869
- Waterfalls beside the road in Crawford Notch at the height of the colour
- The view over Camden harbour and Penobscot Bay from Mount Battie
- Hauling lobster traps on a working boat in Bar Harbor, with seals on the ledges
- Hot popovers at Jordan Pond House, then a horse-drawn carriage on Acadia's carriage roads
- Junior Ranger badges on Cadillac Mountain, then paddling at Sand Beach and the boom of Thunder Hole
- Portland Head Light above the surf on the last morning
What makes this trip different
Short drives, all published
Every drive is listed day by day. The longest is 5 h, on day 3.
Free time is part of the plan
Free time and choices are marked on the days they fall.
Solo without the penalty
A room of your own is + CAD 855 (estimated price).
Day by day
Itinerary
The longest drive is 5 h, on day 3.
Tap any stop on the map to open that dayClick any stop on the map to open that day
Boston to North Conway
Boston Logan airport to North Conway, New Hampshire, about 2 hours 45 minutes
- Welcome dinner
- Stay in North Conway
- Drive about 3 h
Fly into Boston Logan (BOS) by about 11 am, where your See Sight Tours guide meets the family at arrivals and the driver loads the bags into our van, with child seats or boosters ready for the ages you have booked.
Afternoon
We leave the city on Interstate 95, cross the short New Hampshire coast near Portsmouth and turn north on Route 16 through the lakes and woods around Ossipee, stopping halfway for lunch on your own and a stretch. As the road climbs, the maples on the hillsides turn from green to orange and red. By mid-afternoon we reach North Conway, a small town in the Mount Washington Valley, and check in to the hotel for two nights. There is time for a swim if the hotel has a pool, or a walk along the main street to the old railway station of 1874.
Evening
The welcome dinner starts at about 5:30 pm, so the youngest guests are in bed on time.
Included
- Pick-up at Boston Logan airport (BOS)
- Welcome dinner at about 5:30 pm
Easier option: Rest at the hotel after the drive.
More active option: Walk the length of North Conway's main street to the railway station.
Free time: Late afternoon free at the hotel
Activity: Land at Boston Logan by about 11 am. Lunch is on your own at the halfway stop.
The Cog Railway up Mount Washington
North Conway through Crawford Notch to the Cog Railway base station and back, about 1 hour 15 minutes each way
- Breakfast and lunch
- Stay in North Conway
- Drive about 2.5 h
Morning
After breakfast we drive about 1 hour 15 minutes through Crawford Notch, a steep pass where the road runs below granite cliffs and the colour is often at its brightest in early October, to the base station of the Mount Washington Cog Railway. It has carried passengers to the summit since 1869. The train climbs three miles of track, with grades as steep as 37 percent, over the curved trestle called Jacob's Ladder and above the tree line onto bare rock. At 6,288 feet (1,917 m), Mount Washington is the highest peak in the northeastern United States, and on a clear day the view reaches into four states and Quebec. The round trip takes about three hours, with about an hour at the top, all of it seated except the summit. Summit trips run only when the weather allows.
Afternoon
Lunch is near the base. On the way back we stop at Silver Cascade and Flume Cascade, two waterfalls a few steps from the road, and are back in North Conway by about 4 pm.
Included
- Mount Washington Cog Railway round trip to the summit, weather permitting
- Lunch near the base station
- Crawford Notch with stops at Silver Cascade and Flume Cascade
Optional experiences
- The Conway Scenic Railroad Valley train from North Conway, about an hour in vintage coaches, in the late afternoon if the timetable allows (price shown at booking)
Easier option: Stay in the warm summit building at the top, and view the waterfalls from the van-side pull-offs.
More active option: A short scramble on the rocks around the summit with the guide, weather permitting.
Free time: Late afternoon free from about 4 pm for the pool or the optional train
Activity: Warm layers, hats and gloves for the summit, even for children who say they are not cold.
Freeport, Camden and on to Bar Harbor
North Conway to Freeport, about 1 hour 45 minutes, Freeport to Camden, about 1 hour 20 minutes, then Camden to Bar Harbor, about 1 hour 50 minutes
- Breakfast and lunch
- Stay in Bar Harbor
- Drive about 5 h
Today crosses Maine from the mountains to the sea. It is the longest day of the trip, about 5 hours of driving in all. It means three hotels instead of four, and we break it into three legs of under 2 hours each. We leave North Conway at about 8 am and drive about 1 hour 45 minutes by Route 302 and Interstate 295 to Freeport, for toilets, a snack and a photo with the giant boot outside the L.L.Bean flagship store. From there the coast road, US Route 1, takes about 1 hour 20 minutes to Camden. A short road climbs Mount Battie in Camden Hills State Park to a stone tower and a view over the harbour, the schooners and the islands of Penobscot Bay; the poet Edna St. Vincent Millay wrote about this view, and a plaque at the top quotes her.
Afternoon
Lunch is in the town by the harbour, with time to watch the boats. After lunch we follow the coast through Belfast and Bucksport onto Mount Desert Island, about 1 hour 50 minutes, reaching Bar Harbor by about 4:30 pm.
Evening
Dinner is on your own tonight.
Included
- A stop in Freeport at the L.L.Bean flagship store
- Mount Battie summit and tower, Camden Hills State Park
- Lunch in Camden
- A walk along Camden harbour
Easier option: The Mount Battie road goes to the top, so the view needs only a few steps from the van.
More active option: Climb the stone tower on Mount Battie for the higher view.
Free time: Evening free in Bar Harbor
Activity: The longest drive of the trip, about 5 hours, in three legs of under 2 hours each, broken by Freeport and by lunch and Mount Battie in Camden.
Lobster boat, popovers and carriage roads
Bar Harbor, Jordan Pond and Acadia's carriage roads, about an hour of driving
- Breakfast, lunch and dinner
- Stay in Bar Harbor
- Drive about 1 h
Morning
The morning starts on the water. A working lobster boat takes the group out of Bar Harbor for a little under two hours on Frenchman Bay, and the captain hauls a few traps, measures each lobster with a brass gauge and explains why the small ones and the egg-carrying females go back. Children can usually hold one. Harbour seals often rest on the ledges.
Afternoon
Lunch is at Jordan Pond House inside Acadia National Park, where hot popovers with strawberry jam have been served since the late 1800s, on the lawn above the pond with the two rounded hills called the Bubbles at the far end. Then a horse-drawn carriage takes everyone for an hour along the broken-stone carriage roads that John D. Rockefeller Jr. built across the island, over stone bridges and through the woods. We are back in town by about 3 pm: time for the pool, a nap or ice cream on the waterfront.
Evening
The lobster dinner is at about 5:30 pm.
Included
- Lobster boat trip on Frenchman Bay, about 1 hour 45 minutes
- Acadia National Park entry
- Junior Ranger booklets for the children, to work on over two days
- Lunch with popovers at Jordan Pond House
- A 1-hour horse-drawn carriage ride on the carriage roads
- Lobster dinner at about 5:30 pm
Easier option: Sit in the boat's cabin out of the wind, and stay on the Jordan Pond House lawn instead of walking to the shore.
More active option: Walk part of the level path around Jordan Pond after lunch, about 1.5 km out and back.
Free time: Afternoon free from about 3 pm
Activity: Warm, windproof layers for the boat.
Acadia's coast and on to Portland
Bar Harbor to Cadillac Mountain, Sand Beach and Thunder Hole, then Portland, about 4 hours with a break halfway
- Breakfast, lunch and dinner
- Stay in Portland
- Drive about 4 h
We enter the Park Loop Road early, at about 8 am, on our timed vehicle reservation and drive up Cadillac Mountain, at 1,530 feet the highest point on the Atlantic coast of the United States, for the view over Bar Harbor and the islands. Children finish the Junior Ranger booklets they started yesterday, and the guide swears them in. Next is Sand Beach, where the children can run on the sand and paddle in the cold water, and the level Ocean Path to Thunder Hole, where waves boom into a slot in the rock when the tide is right.
Afternoon
Lunch is back in Bar Harbor at about 11:30. This is the second long day: we leave at about 12:30 and drive about 3 hours 15 minutes to Portland by Interstate 95, with a 20-minute break at a service plaza about two hours in.
Evening
We check in at about 4 pm, with an hour for the pool or a rest, and the farewell dinner is in the Old Port at about 5:30 pm, with a short walk along the wharves afterwards.
Included
- Cadillac Mountain summit with the vehicle reservation
- Junior Ranger swearing-in for the children
- Sand Beach, the Ocean Path and Thunder Hole
- Lunch in Bar Harbor
- Farewell dinner in the Old Port at about 5:30 pm, and a short walk along the wharves
Easier option: Ride the van between Sand Beach and Thunder Hole instead of walking the Ocean Path.
More active option: Walk the whole Ocean Path from Sand Beach to Otter Point, about 3 km one way, and meet the van there.
Free time: About an hour at the Portland hotel before dinner
Activity: Thunder Hole is loudest about one to two hours before high tide, so the order of the morning may follow the tide table.
Portland Head Light and Boston
Portland to Portland Head Light, then Boston Logan airport, about 2 hours
- Breakfast
- Drive about 2 h
Morning
The last morning is short and easy. After breakfast we drive about 15 minutes to Cape Elizabeth and Fort Williams Park, where Portland Head Light, first lit in 1791, stands above the surf. There are level paths along the cliff top, cannon and old fort walls for the children to explore, and a small museum in the keeper's house, open in the fall on days we confirm when we book. Grandparents can watch the waves from a bench by the van. We leave at about 11 am and drive south on Interstate 95, past the beaches of southern Maine and Portsmouth in New Hampshire, to Boston Logan, about two hours. We plan to reach the terminals at about 1 pm, so book a flight leaving after 3 pm, or later for an international flight. If you want more time, ask us about extra nights in Portland or Boston before or after the trip; Boston's science museum and aquarium suit all three generations.
Included
- Portland Head Light and Fort Williams Park, and the lighthouse museum when it is open
- Drop-off at Boston Logan airport (BOS)
Easier option: Watch the lighthouse and the waves from a bench a few steps from the van.
More active option: Walk the cliff path through Fort Williams Park to the old fort and back, about 2 km.
Free time: An unhurried morning at the lighthouse
Activity: Book flights leaving after 3 pm, later for international flights.
- Bostonstart
- North Conway2 nights
- Bar Harbor2 nights
- Portland1 night
- Bostonend
- Overnight stop
- Day trip
- By boat or train
Wildlife and weather: Late September and early October bring crisp days, with afternoon highs of roughly 13 to 18°C (55 to 65°F) in the valleys and on the coast, cold nights in the mountains, and ice or even snow possible on the summit of Mount Washington. The sea is too cold for most people to swim, so beach time is for paddling and running on the sand. Harbour seals and seabirds are likely from the lobster boat. Moose live in the White Mountains but are not often seen from the road.
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Before you book
Right for you?
Good for you if you want
- Grandparents, parents and children aged 6 and up travelling together
- Families who want someone else to plan the timing, the driving and the meals in the busy foliage weeks
- Grandparents who walk well on the flat but do not want long climbs
- Children who like trains, boats, lobsters, lighthouses and a pool at the end of the day
- A grandparent travelling with one grandchild who wants a fair room price
Not for you if you want
- Families with children under 6
- Keen hikers looking for long trail days
- Travellers who want a Boston city break; add nights before or after
- Anyone who needs a guarantee of peak colour on a given date
- Travellers who want grand resort hotels; see our New England Fall Colours and Acadia trip
Minimum age: 6
Most guests are 6 to 80
Book flights after we confirm your seat.
5 nights
Where you'll stay
Your hotels are named in your trip confirmation.
- North Conway2 nights
- Bar Harbor2 nights
- Portland1 night
One price
What's in the price
Included
Accommodation
- 5 nights: 2 in North Conway, 2 in Bar Harbor and 1 in Portland
- Hotels of a 3-star-plus standard with private bathrooms; we name each hotel when we confirm your dates
- Family rooms or connecting rooms requested for each family, and an indoor pool asked for, both confirmed with your dates
- Rooms shared, or your own for a supplement
Transport
- Pick-up at Boston Logan airport (BOS) on day 1 and drop-off there on day 6, at set group times
- Our own van and professional driver for the group throughout, with fuel, parking and tolls, and child seats or boosters where the law requires them
- The Mount Washington Cog Railway round trip
- A lobster boat trip on Frenchman Bay
Your guide
- A See Sight Tours guide with the group from the day 1 pick-up to the day 6 drop-off
- The lobster boat's captain and the carriage driver in Acadia
Activities
- Mount Washington Cog Railway to the summit, weather permitting
- Crawford Notch, Silver Cascade and Flume Cascade
- Mount Battie and Camden Hills State Park entry
- Camden harbour
- Acadia National Park entry and the Cadillac Mountain vehicle reservation
- A Junior Ranger booklet for each child, and the swearing-in
- A 1-hour horse-drawn carriage ride on Acadia's carriage roads
- Sand Beach, the Ocean Path and Thunder Hole
- A stop in Freeport
- Portland Head Light and its museum, Fort Williams Park
- An evening walk in Portland's Old Port after the farewell dinner
Meals
- 5 breakfasts
- 4 lunches: near the Cog Railway, in Camden, popovers at Jordan Pond House, and in Bar Harbor on day 5
- 3 dinners at about 5:30 pm: a welcome dinner in North Conway, a lobster dinner in Bar Harbor and a farewell dinner in Portland
Not included
- Flights to and from Boston
- Travel insurance
- Passports, and an ESTA or US visa where needed
- Lunches on days 1 and 6, and dinners on days 2 and 3
- Drinks
- Tips for your guide, driver, boat captain and carriage driver
- Optional activities, such as the Conway Scenic Railroad
- Personal expenses
- Hotel nights before day 1 or after day 6
Extras
- Room of your own
- CAD 855 (estimated price)
When you can go
Dates and prices
Pick your start date when you request to book. We check that date and confirm it in your quote.
Prefer to travel without a group or guide? Ask us about arranging hotels, transport and city tours for you to travel independently.
Before you book
Booking terms
Nothing is charged now. Full terms and the cancellation schedule come with your quote, before you accept.
Business addresses
See Sight Tours Trips (USA): 3172 N Rainbow Blvd, Las Vegas, NV 89108, United StatesSee Sight Tours Trips (Canada): 5305 50 Avenue, #1091, Red Deer, AB T4N 4B6, Canada+1-888-961-6584Guest reviews
What guests say
Reviews from guests on our day tours.
Jane
October 06, 2026
5/5
Susan
October 06, 2026
5/5
Tom L
October 05, 2026
5/5
MandL83
October 05, 2026
5/5
Darren O
October 05, 2026
5/5
Good to know
Questions
What does the price include?
Five nights in hotels with family or connecting rooms requested, our van and driver with a See Sight Tours guide from Boston Logan and back, the Mount Washington Cog Railway, Acadia entry, a lobster boat, a carriage ride, Junior Ranger booklets, Mount Battie and Portland Head Light, with 5 breakfasts, 4 lunches and 3 early dinners. Flights, drinks and tips are extra.
What age do children need to be?
Children need to be 6 or older. The days are built so a 6- to 12-year-old and a grandparent in their 70s can do the same plan, with short walks, seated train and boat rides, and an easy option every day. Teenagers usually enjoy the summit, the lobster boat and the active options.
Is there a price for children?
Children pay the shared-room price for now. A reduced price for children aged 6 to 15 sharing a room with adults is something we quote on request when you send your dates and the ages, because it depends on the room types each hotel can hold for your family.
How big is the group, and will we be with other families?
Departures run with 7 to 12 guests, counting children, so a family of seven or more can fill a departure on its own. Otherwise you travel with other three-generation families. One See Sight Tours guide and a professional driver travel with the group from Boston to Boston.
How much walking is there for grandparents?
Very little that is hard. Walks are 1 to 3 km a day on level paths, boardwalks and town streets. The Cog Railway and the Mount Battie road do the climbing, the van is always close, and the uneven granite on the Ocean Path can be skipped by riding between viewpoints.
How long are the drives?
Four of the six days have 3 hours or less in the van, in legs of about 2 hours or less. Two days are longer: day 3, about 5 hours across Maine in three legs broken by Freeport and lunch in Camden, and day 5, about 4 hours, with Acadia in the morning and a break halfway to Portland.
I am a grandparent travelling with one grandchild. What is the single supplement?
A grandparent sharing a room with a grandchild pays no supplement; both pay the shared-room price. An adult who wants a room alone pays CAD 855 more, shown before you book. A solo adult who would like to share can ask us to find a roommate on the same departure; if no match is found, the supplement applies.
When does the trip run, and will the leaves be at their peak?
Departures run from late September to mid-October, the usual peak for the White Mountains with the Maine coast a little later. The exact week shifts every year, so no one can promise it. A departure across the October long weekend, Thanksgiving in Canada and a holiday in the US, saves school days.
What happens if the weather closes the summit of Mount Washington?
The Cog Railway runs to the summit only when it is safe, and summit trips usually run until late October. If the summit is closed, the railway may run a shorter trip or none that day, and the guide fills the day with Crawford Notch, its waterfalls and, if it suits the family, the Conway Scenic Railroad.
How does booking work?
Send a request to book with your preferred departure, the number of guests and each child's age. We check availability and provide the final quote, itinerary and booking terms before you accept. No payment is taken when you send the request.
Can our family travel privately or on our own dates?
Yes. The private style is your family only, with your own guide and van, on a date you choose in the season, from CAD 8,795 per person. If you would rather travel independently on your own dates, ask us from the dates section for a quote.
Do children need passports to visit from Canada?
Yes. Every Canadian citizen, including children, needs a valid passport to fly into the United States. No visa is needed for a visit. A child travelling with only one parent or with grandparents should carry a signed consent letter from the absent parents.
See Sight Tours has been providing travel services across North America since 2006. Operating in 20 cities across Canada and the USA, the company specializes in small group tours that offer personalized, high-quality experiences for travelers.
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