This reminds me many of the zip around Ireland or Italy itineraries we often see. Not my style, but it’s your trip not. Ine. You know your own family best and if these are the locations you want to fit in that time span, you’ve succeeded and I make no attempt to dissuade you.

You may (or may not) wish to actually map out the hours in a day - I am confident you’ll see that when you factor in driving, meals, border crossings, traffic, bathroom breaks, hotel check in / check out, etc. you’ ll have precious little time to actually enjoy where you are.

That said, for the areas I am most familiar with which is lake george and Lake Placid I think you have ended on a realistic 1-2 day plan in each location. As long as you prioritize, and are ok dropping things due to fatigue, or hanger, or weather then you’ll get to all the places.

As you get closer to your trip, or need local expert tips, feel free to ask and I’ll do my best to give informed answers. I was in Lake George briefly earlier today and always admire the beauty. The water is too cold to swim in but I was tempted to take a polar bear plunge.

Please take these comments as hopefully helpful - not criticisms. I have a hunch that you've glommed on to some ChatGPT/AI itinerary or some Italian travel agent's suggestions and are set on using those ideas (there seems to be a lot of copy/paste going on because of all the bold text). To your credit, you have absorbed/incorporated a few of the suggestions from Fodorites but for the much of this you've have ignored and keep going back to a variation of the original plans. Not that Fodroites are infallible (though we mostly are ) HOWEVER those posting have real world experience in the areas you want to visit and several of them live in those areas. Some of your days have unacceptably long drives -- maybe OK for a single/young couple on a road trip where the driving someplace is more important than actually being anywhere -- but not anything fun/enjoyable for two little girls.

Many of the places you emphasize are really lovely, a few are sort of ordinary -- but some seem to be odd choices for a family's first visit to the USA.

OP- Why do you seem to be set against using public transportation, such as buses or trains or flying from Vermont to Montreal? It so much more convenient and you’re not sitting in a car. Aside from which I highly doubt ANY American car rental company gives permission for their vehicles to be across the northern border. It’s just not happening. Then we’ve got the issue with the whole one night in Boston and then two nights on the Cape. You don’t say where in Boston because it’s pretty large, for New England that is. Then, you’ll be driving to Cape Cod, at the height of summer and then driving to NYC! Did you know that at that time of the year it can take more than 4 hours to drive from the Cape to NYC? Believe me, as a native NYer who’s lived in this area for close to 15 years I’ve only flown to NYC since 2018. It’s not worth the hassle of driving. Add in kids and it’s a nightmare just fly/bus/train between places. It’ll make your trip that much more enjoyable because two weeks is definitely NOT enough time to visit these places driving. Impossible.

If you are making the trip down to Montreal go the extra hour and half to Mont Tramblant your daughter will really enjoy it there.
Every major US car rental allows taking their cars into Canada some might have exceptions for very luxurious cars

I did a roadtrip from NYC through New England for 4 nights. I suggest a loop, although Montreal is the most out the way so if you're gonna nix a spot, i'd suggest that one. That way you can enjoy driving the slower, scenic byways. Google "scenic byways for each state and you'll get the official brochure pdf that'll help you map out a beautiful route.

AUGUST 1 – NEWARK LIBERTY → JERSEY CITY / HOBOKEN

Total: ~17 km – 15 min

• Newark Liberty International Airport arrival
Arrival at 9:00 PM – Terminal B

• Transfer to hotel in Jersey City

AUGUST 2 – JERSEY CITY → MANHATTAN

Total: ~27 min by PATH train

• Manhattan
• Times Square

AUGUST 3 – JERSEY CITY → CENTRAL PARK → PHILADELPHIA

Total: ~147 km – 1h40 by train (or evaluate if Irene comes and leave the car in Jersey City)

• Brooklyn Bridge
• Central Park
• Transfer to Philadelphia

AUGUST 4 – PHILADELPHIA

• Full day in Philadelphia with my sister

AUGUST 5 – PHILADELPHIA → STOCKBRIDGE

Total: ~422 km – 4h47

• Alamo Rent A Car FORD EXPLORER
1 Arrivals Rd, Philadelphia, PA 19153
Car pickup at 10:00 AM

• Woodbury Common Premium Outlets
2h23 – Famous outlet with hundreds of stores

• Walkway Over the Hudson State Historic Park
61 Parker Ave, Poughkeepsie, NY
44 min – 66 km
Walk on the historic bridge

• Home of Franklin D. Roosevelt National Historic Site
4097 Albany Post Rd, Hyde Park, NY
18 min – 13.8 km
Historic estate, grounds and buildings

• Vanderbilt Mansion National Historic Site
119 Vanderbilt Park Rd, Hyde Park, NY
7 min – 4 km
Historic mansion

• Bash Bish Falls
Mount Washington, MA
59 min – 67.7 km
Waterfall in Bash Bish Falls State Park

• Stockbridge, Massachusetts
36 min – 32.4 km
Picturesque historic New England village

AUGUST 6 – STOCKBRIDGE → WOODSTOCK / KILLINGTON

Total: ~249 km – 3h33

• Jamaica State Park
48 Salmon Hole Ln, Jamaica, VT
1h54 – 153 km
State park along the West River, swimming holes, waterfalls, picnic areas

• Woodstock, Vermont
2h45 – 210 km
VT Route 100 (scenic drive from Londonderry onward)
Quechee Gorge
Sugarbush Farm
Marsh-Billings-Rockefeller National Historical Park

AUGUST 7 – WOODSTOCK / KILLINGTON → STOWE

Total: ~194 km – 2h37

• Warren Falls
3919 VT Route 100, Warren, VT
53 min – 60 km
Natural pools and waterfalls, short walk from parking

• Historic Village Covered Bridge
Bridge St, Waitsfield, VT

• Burlington, Vermont
1h – 76 km
On Lake Champlain, views of the Adirondacks
Waterfront and Church Street Marketplace

• Stowe, Vermont
44 min – 58 km
Ben & Jerry’s Factory (on the way)
Moss Glen Falls (7 min from Stowe, 1.6 km walk)
Bingham Falls (11 min from Stowe, 400 m walk)

AUGUST 8 – STOWE → LINCOLN

Total: ~148 km – 1h49

• Lincoln, New Hampshire

The Basin – small natural granite pool and waterfalls (15–20 min easy walk)
Flume Gorge – granite canyon with wooden walkways and waterfalls
Kinsman Falls – smaller scenic waterfall, short walk from parking

AUGUST 9 – LINCOLN → BRIDGTON

Total: ~93.8 km – 1h25

• Sabbaday Falls
Waterville Valley, NH
30 min – 30 km
Most famous waterfall in the area, easy access

• Rocky Gorge Scenic Area
Kancamagus Highway, NH
9 min – 10 km
Natural pool among rocks and rapids, 10–15 min walk

• Lower Falls Recreation Site
Kancamagus Highway, Conway, NH
3 min – 3.4 km
Wide scenic waterfall, 5–10 min walk

• Bridgton, Maine
44 min – 49.3 km
Overnight stop

AUGUST 10 – BRIDGTON → MILLINOCKET

Total: ~339 km – 4h

• Grocery shopping and early night

AUGUST 11 – MILLINOCKET → MILLINOCKET

• Millinocket → Togue Pond Gate (30 min)
• Togue Pond Gate → Daicey Pond
16.7 km – 35–40 min

Daicey Pond: postcard views, Mount Katahdin in front.
Optional walk to Big & Little Niagara Falls (~1 mile each way, 1.5–2h, easy).
Possibility to rent a canoe or kayak.

• Daicey Pond → Roaring Brook Campground (Sandy Stream Pond)
20–22 km – 40–45 min

Sandy Stream Pond Trail: 0.8 km total, very easy.
Moose spotting area.

Planned strategy to increase chances of seeing moose:
05:30–06:00 – Arrival at Togue Pond Gate
Ask immediately for Moose Pass
Drive directly to Sandy Stream Pond
06:30–07:00 – Arrival at Sandy Stream Pond

• Roaring Brook → Togue Pond Gate (exit)
15 km – 30 min
• Togue Pond Gate → Millinocket
30 min

AUGUST 12 – MILLINOCKET → BAR HARBOR

Total: ~195 km – 2h15

• Acadia National Park ($35 per vehicle)
Park Loop Road – 32 km scenic loop

• Cadillac Mountain (if booked)
Vehicle reservation required ($6)
Preferably sunset time
Summit Loop Trail at the top

AUGUST 13 – ACADIA NATIONAL PARK

• Sand Beach
• Ocean Path (3.5 km one way, Sand Beach to Otter Point)
• Thunder Hole
• Otter Point
• Jordan Pond Path (loop trail around the lake)
• Bar Harbor

AUGUST 14 – BAR HARBOR → KENNEBUNKPORT

Total: ~368 km – 5h30

• Marshall Point Lighthouse
Port Clyde
2h28 – 165 km
Famous from the movie Forrest Gump

• Sea Basket
303 Bath Rd, Wiscasset, ME
1h – 71 km
Classic New England lobster roll

• Portland Head Light
Cape Elizabeth, ME
1h – 80 km
Oldest and most iconic lighthouse in Maine

• Kennebunkport, Maine
46 min – 50 km

AUGUST 15 – KENNEBUNKPORT → COAST → BOSTON

Total: ~164 km – 2h45

• Nubble Light / Sohier Park
York, ME
36 min – 30 km

• Kittery Premium Outlets
21 min – 9.7 km

• Salem, Massachusetts
55 min – 80 km
Essex Street
Salem Witch Trials Memorial
Salem Common
Salem Witch House

• Boston, Massachusetts
42 min – 35 km

AUGUST 16 – BOSTON

• Freedom Trail
Boston Common
Massachusetts State House
Park Street Church
Old State House
Faneuil Hall
Quincy Market

AUGUST 17 – BOSTON → NEWPORT

Total: ~114 km – 1h30

• Newport, Rhode Island
Ocean Drive
Fort Adams State Park
Bowen’s Wharf
Historic mansions
Cliff Walk

AUGUST 18 – NEWPORT → GREENWICH

Total: ~234 km – 2h36

• Greenwich, Connecticut
Last quiet night near JFK
Hotel, pool, parks, seaside walk

AUGUST 19 – GREENWICH → JFK

Total: ~55 km – 1h

• JFK International Airport
Terminal 1

Sorry for the long absence, but I had to study.
I’m posting my final itinerary below. Let me know what you think.

I included several attractions on some days to give myself flexibility and the possibility to choose on the spot depending on energy, weather, and daily needs. I don’t plan to do everything for sure.

This trip is meant to be a road trip, and that’s exactly what we are looking for. Please don’t judge the itinerary based on a “do everything / see everything” logic — driving, changing scenery, and enjoying the journey itself is part of our goal.

Apart from hotels, I won’t book much in advance.

bro you got a solid plan already not gonna lie the east coast aint the grand canyon but its still beautiful in its own way especially in august when everything is green and lush

lake george is gonna be fire for the kids they can swim and do boat stuff and its super scenic with the mountains around it the adirondacks are underrated honestly just drive the roads and stop at random lakes your daughters will love it

montreal is a vibe feels like europe honestly so you might actually feel at home there get some poutine and walk around old montreal its beautiful

vermont is where it gets real scenic for real the green mountains are no joke take route 100 if you can its one of the prettiest drives in america and theres little towns with ice cream shops and covered bridges the kids will be all over that

acadia is the highlight though im not even gonna cap thats gonna feel like the national parks you loved out west but east coast style cadillac mountain at sunrise hits different and bar harbor is cute for walking around and eating lobster

portland maine is lowkey amazing for food even if youre with kids the waterfront is chill and you can do a lighthouse tour or whatever

boston is boston do the freedom trail if the kids are into history or just walk around and get cannolis in the north end

cape cod might be a lot with everything else youre doing so if you gotta cut something maybe skip it or just do one day there the beaches are nice but youve already got beaches in italy you know

honestly your loop is ambitious but doable just dont rush it and enjoy the vibes the east coast is more chill than dramatic but its still beautiful especially with family

have a good trip my guy

I think you have a well thought out road trip as you’ve intended.

Beware of driving time estimates through cities. For example, your drive from Greenwich to JFK might only take an hour, but it could easily be far more than that.

August 14 is not enough time to see Maine ntween Bar Harbor and Kennebunkport. You’ve missed the view from the top of Mt Battie in Camden (take the auto road). We’ve eaten several times at the Sea Nasket since we used to camp in Wiscsset. It’s decent for a roadside casual restaurant but the lobster rolls always seem to taste better if you can be looking at the ocean. Our favorite is McLoon’s in S. Thomaston near Rockland. If you want something closer to Rt 1, Claws in Rockland has covered porch dining overlooking the harbor.
it was our family tradition to visit York Beach and the amusement park. It is also obligatory to watch the taffy pulling machine at the Goldenrod and buy some saltwater taffy.
can you find time to take a boat ride?

I would get Ben and Jerry’s ice cream someplace else. Imthink your children would like the Teddy Bear factory better.

The Flume is great. You can see NH native animals at Squam Lakes Science Center. The indoor lectures can be exciting. We met an Eastern coyote.

The nesr water play in addition to VT rocky streams is the Montshire Museum in Norwich. You can visit the museum in the morning, have a picnic lunch, have children change into bathing suits and visit the outdoor water play area.

I would cut down number of stops and spend more time at the best ones.

This entire trip of yours reads like it was written by AI or just copied and pasted right off Google maps. I mean no offense but every single post of yours about this upcoming trip of yours, in August, makes zero effort to take into account certain facts, such as, that it’ll take a heck of a lot more than 4 hours and 47 minutes to drive from Philly to Stockbridge. It’s August, the height of summer and tourist season, especially in the Berkshires, or anywhere on the East Coast for that matter.
One hour from Boston to Newport? I couldn’t make it that fast even at 2 am with clear roads. Remember, every single driving time will be, at best, doubled or even tripled in some cases because of the fact that it’s August. I understand wanting to do a road trip, we’ve all fantasized about it, but to do it in August, in the East coast, not allowing for extra travel time due to it being August, is a recipe for disaster.
Greenwich CT—->JFK, one hour? Never heard of such a short travel time. It’ll take an hour just to get from Greenwich to the major highway intersections near NYC. In case you’re unaware but there’s MAJOR construction works going on at JFK that probably won’t finish until 2029, if we’re lucky. JFK is difficult to navigate without all the works going on. With it, it’s an absolute nightmare.
in essence, I really cannot suggest anything for you on your trip as you seem dead set against taking any advice any of us have given you. Taking your car into Boston? You haven’t said where in Boston you’ll be staying. All I see are driving times that don’t seem logical or set in reality. Trust me, as one who’s done the drive from Cape Cod to NYC 30 times over 5 years, before I realized that it’s less stressful to fly, the shortest time it took me from the Cape was 4 hours. I’ve driven all over MA, VT, NH, ME, CT and I can unequivocally tell you that it always takes longer to get places than what Google maps will tell you, again, especially if one is doing that driving at the height of summer travel.
Buona fortuna e buon viaggio.

Thank you so much for your feedback, it’s really helpful!
Regarding August 14, I’m not sure if I’ll be able to fit in the view from the top of Mount Battie in Camden, but I’ll definitely consider it. Unfortunately, as this is a road trip, I had to make some tough choices and the beautiful spots are quite spread out. I’ve rented a car specifically for that flexibility, so there will be some longer stretches between destinations.
I really appreciate the tip about the Teddy Bear Factory, it’s a great suggestion! I chose Ben & Jerry’s mainly because it’s more on the route and saves a bit of time.
I’d love to focus more on the really nice spots and stay longer in fewer places, but given the distances, it’s a bit tricky. If you have any tips on how to streamline the itinerary even more, I’d really appreciate it.
Thanks again!

Thank you for taking the time to write such a detailed response.I really appreciate the heads-up about the driving times in August. I completely understand that the actual travel times will likely be much longer than what Google Maps shows.I want to clarify that this itinerary is far from a simple copy-paste or AI-generated plan. It’s the result of months of research, including books about New England, blogs by other Italian travelers, and suggestions from this very forum.I’m an Italian from Milan, and I’ve lived in Utah for a while, but I’m not familiar with the East Coast. I’m doing my best to get accurate info, and I do rely on Google Maps for distance and time estimates, knowing they’ll vary in summer.Ultimately, if the places I want to visit are far apart, I have to accept longer drives. I’ll adjust as I go, and if I find that some stops aren’t feasible, I’ll skip them.I’m absolutely open to any practical suggestions you might have on how to streamline the itinerary and make it more realistic.Thanks again for your input, and I’ll definitely keep it in mind!

Much better itinerary and glad you are aware that your timing are all for optimal conditions. Optimal conditions are not the usual conditions that most of us experience when traveling in the Northeast in August but you will certainly be covering quite a lot of ground.

DO NOT rely on Google maps for estimated driving times. It will ALWAYS be wrong. Nice to see you’ve fixed your travel plans. Yes, I understand it’s a road trip, but not all road trips HAVE to be driving only. Utah, eh? That must’ve been a culture shock being from Milano. Anyway, enjoy your trip, and happy travels!

Agree with other posters as virtually impossible to drive from Greenwich to JFK in one hour as that would only work if there were zero cars on the road as that route is heavily traffic with trucks as well as other cars, having driven this way zillions of times in my life

What would be a realistic driving time, based on your experience?

I don’t know what time your return flight is but you need to arrive at JFK 3 hours before and I would assume a 2 hour drive plus you need to deal with rental car return. I’ve never returned a rental car at JFK as I am usually heading straight home.

Thank you