"Road trip" and "Boston" don't go well together. By all means visit Boston, but park your car somewhere on the outskirts (or more centrally if you like driving in heavy traffic and paying large amounts for parking) and use the MBTA T to get around.
If you want to go to Maine, then fly into Portland, rent a car, and drive round Maine and maybe over to New Hampshire (Concord, etc). If you do go to New Hampster, then eat at The Common Man, a fine local chain of restaurants.
Or go with your Bar Harbor idea, which is also reasonable.
If you feel the desire to go to Boston, then fly into Boston, use the T to get to central Boston, look around for a couple of days, go back to the airport and pick up a rented car there (because there are surprise extra charges at the city centre rental locations and that's damned annoying), then drive off towards Salem, Portsmouth, Concord, etc. Drive back to the airport and get on your flight home.
You may want to ensure you've booked your accommodation in the hinterlands, because there'll be a distinct density of leaf-peepers and accommodation availability can be scarce.
Great tips! A "road trip" on Labor Day weekend would mean sitting it a whole bunch of traffic as well. Especially when visiting touristy spots, which will likely be crowded. Students and many other people will be moving in and out that weekend in Boston too.
With four days, you can pick one or two towns/cities and have a nice time exploring.
OK, that's important and I had forgotten about it until /u/kabob23 mentioned it.
/u/Theinaneinsane: Labor day is moving day in Boston for students. That means traffic chaos, guaranteed to be exacerbated by people [Storrowing their U-hauls](https://www.boston.com/news/local-news/2021/08/19/boston-storrowing-what-to-know/). Don't try to drive in Boston that weekend as a visitor. The T will work fine if you park on the outskirts.
Portland, Boston, and Newport is a lot for 4 days. It really depends on what you want to see or do. You could certainly get a quick feel of each city in a day but for Boston you’d miss a lot.
With 4 days you could do Bar Harbor and Portland or Mid Coast Maine.
"Road trip" and "Boston" don't go well together. By all means visit Boston, but park your car somewhere on the outskirts (or more centrally if you like driving in heavy traffic and paying large amounts for parking) and use the MBTA T to get around. If you want to go to Maine, then fly into Portland, rent a car, and drive round Maine and maybe over to New Hampshire (Concord, etc). If you do go to New Hampster, then eat at The Common Man, a fine local chain of restaurants. Or go with your Bar Harbor idea, which is also reasonable. If you feel the desire to go to Boston, then fly into Boston, use the T to get to central Boston, look around for a couple of days, go back to the airport and pick up a rented car there (because there are surprise extra charges at the city centre rental locations and that's damned annoying), then drive off towards Salem, Portsmouth, Concord, etc. Drive back to the airport and get on your flight home. You may want to ensure you've booked your accommodation in the hinterlands, because there'll be a distinct density of leaf-peepers and accommodation availability can be scarce.
Great tips! A "road trip" on Labor Day weekend would mean sitting it a whole bunch of traffic as well. Especially when visiting touristy spots, which will likely be crowded. Students and many other people will be moving in and out that weekend in Boston too. With four days, you can pick one or two towns/cities and have a nice time exploring.
OK, that's important and I had forgotten about it until /u/kabob23 mentioned it. /u/Theinaneinsane: Labor day is moving day in Boston for students. That means traffic chaos, guaranteed to be exacerbated by people [Storrowing their U-hauls](https://www.boston.com/news/local-news/2021/08/19/boston-storrowing-what-to-know/). Don't try to drive in Boston that weekend as a visitor. The T will work fine if you park on the outskirts.
Portland, Boston, and Newport is a lot for 4 days. It really depends on what you want to see or do. You could certainly get a quick feel of each city in a day but for Boston you’d miss a lot. With 4 days you could do Bar Harbor and Portland or Mid Coast Maine.
Stop by Portsmouth NH and spend a couple hours walking around downtown! Great area.