Philly to PEI

We live in Moncton, New Brunswick, which would be right on your scenic route from Bangor to PEI.

Mid-September is very nice. You will see the beginning of the leaves turning. Maybe lean toward later September if your calendar will allow.

The drive from Bangor to PEI would be about 6 hours plus stops. You have a choice of two routes from Bangor to Moncton, and two routes from Moncton to PEI.

Bangor-Moncton (more scenic): State Route 9 to the border at Calais ME, then NB Rte 1 to Moncton. This is called the Airline (for apocryphal reasons). It will take you near beautiful Saint Andrews (but you'll have to exit off a few miles). You'll see the Bay of Fundy (and pass over the Reversing Falls in Saint John where the tides come in so high they actually push a rapids uphill).

Moncton-PEI (more scenic): NB Rte 15 to Shediac. After Shediac, get off the main highway and use NB Rtes 133, 950 and 955 to follow the Northumberland Strait coast all the way to the Confederation Bridge to PEI.

Bangor-Moncton (less scenic but easier drive): I-95 to Houlton Maine, then Trans-Canada Highway to Moncton. Four lanes the whole way. You'll see Mt Katahdin in Maine a way off in the distance, but otherwise its a dull road.

Moncton-PEI (less scenic but easier drive): Stay on NB Rte 15 all the way from Moncton, past Shediac, until you get to the Trans-Canada Highway again just before the Bridge.

If you fly to Halifax, then you would drive to the ferry at Caribou, Nova Scotia (near Pictou). The drive itself isn't much unless you use the parallel local highways, but the ferry is a nice ride.

I am surprised to hear flying direct to PEI from the US is even an option. I would have thought you would have to connect in Halifax. And if you do have to fly through Halifax, I would just as soon drive as connect. It won't take you much longer (maybe even faster, depending on the connection), and you'll have the scenery en route.

You don't say how much time you are spending on your holidays but from Philly to Charlottetown you are looking at about 17 hours on the road. Unless you really like road trips (we do) I would save the time and fly to Halifax, rent a car and drive to PEI in 3 hours, not including ferry wait time and the crossing time.

We have driven the routes mentioned by the previous poster and they are as described, nice but not memorable.
We were in PEI last summer and loved it.

We drove from an overnight stop in Bangor to Saint John, then Halifax, and PEI. Maine Highway 9 from Bangor to Canada is not a very interesting drive. As one former president (of the US) was said to say, you've seen one tree you've seen them all. Highway 9 has a lot of trees and very few view scenic pullouts or views. If we weren't visiting Mainers, flying to Halifax would have been a better use of time and driving miles.

As someone who has driven the Nova Scotia to Maine and points south a few times - the drive from past Bangor to the NB border is hella boring - Rt 9 isn't as bad, because it isn't a twinned highway, so it holds your attention a little more, but we found it lightly travelled and passing lanes are pretty frequent, and there are some nice sections. The I95 is just a boring old twinned highway thru trees and trees and more trees. And the drive thru New Brunswick could put an insomniac to sleep. (There are a few beautiful spots where you are driving thru a valley, but that's it). For the record, we usually go to the St Stephens border crossing, but have used the Houlton one a few times - time diff is negligible.

Not that the drive from Halifax is much more scenic. If you wanted to take your time, you could take some of the old highways. If you were going to take the Confederation bridge over to PEI (for the record, you only pay when LEAVING PEI, and the bridge is cheaper than the ferry), you could bypass the toll section of the highway between Debert and Oxford and take the 'old' hwy 4 thru Folly Lake and Wentworth. It's quite pretty in the autumn. My mom and I did that drive last year (but we detoured to Tatamagouche) in the latter half of Oct. If you want to take the ferry over, I'd just stick with the 104 until you get to the exit for the ferry.

Mid Sept to mid Oct is my fav time of year - the weather is generally still warm enough for sandals and shirt sleeves. I find for real autumn colour, that the first few weeks of Oct is usually the best. You should still get some colour in mid-Sept, but if you are coming for foliage, you may be better off waiting a few more weeks.

Thank you all for your informative responses. From them I've gathered this:
Travel late September/early October (check).
Fly to Halifax (rather than fly to Bangor then drive to PEI) (check).

Now my question is, once in Halifax, best way to get to PEI?
Should we stay in Charlottetown?
Hotel or Air BnB? (Never did Air BnB - any suggestions or comments?)
Best sights to squeeze in to our 5-day stay (plus 2 travel days)?
THANKS!

Now my question is, once in Halifax, best way to get to PEI?

Rental car. Drive C'Clockwise free ferry to PEI, return via toll
bridge.

Should we stay in Charlottetown?

The large town offers multiple hotel/motel options with many
restaurant dining options.

Hotel or Air BnB? (Never did Air BnB - any suggestions or comments?)

It seemed like the beach/ocean cottages were closing down by late
September. Question is do you want to self cater meals?

Best sights to squeeze in to our 5-day stay (plus 2 travel days)?

A lot of sightseeing. Are you a Anne of Green Gables fan?
Seafood: New Glasgow Lobster Suppers https://peilobstersuppers.com/
Nice lunch spot, regional food. Take a relaxing walk in the garden
after lunch: https://preservecompany.com/

Once you are in your rental car follow the signs for Cape Breton and until near Pictou you will see signs for the "Ferry to PEI"

Charlottetown makes a great base to explore the Island. There are several quaint B&Bs, live outdoor music, live theatre and some great seafood and chowder.

The city is very walkable and harbour and seal watching tours are available at Peakes Wharf. The New Glasgow Lobsters are highly recommended (see the link above). Live music at night at the Old Triangle and other pubs.

You could spend a day at Cavendish Beach and explore some of the small towns and villages.

Charlottetown is the hub and if you want to be in a city, that is really the only one.

But let me put in a plug for staying in a B&B in one of the smaller villages that dot the island. My favourite village is North Rustico. Its about 20 minutes from Ch'town and 5 minutes from Cavendish (beach, Green Gables). North Rustico has a famous lobster supper and all-you-can-eat salad bar which I just love, fishing excursions from the harbour, and a lighthouse and beach for walking. I've stayed at two different B&B's there. One was called Cois Farrage in nearby Rusticoville, and one was an A-framed house right in North Rustico. You should be able to Google them.

If you do stay in Charlottetown, I can recommend the Rodd Charlottetown Inn and the Inn at Great George Street. There is a Delta hotel too if you want a business-style hotel.

If you really want the backwoods experience, take 95 from Bangor, get off 95 and drive through Lincoln to Route 6. Cross the border in Vanceboro, ME to McAdam, NB then to Fredericton and PEI. It's about the same amount of time and the border crossing doesn't back up like it sometimes does in Calais (Pronounced callous)/St. Stephens. And you will see more trees and fewer houses than you ever thought possible.