My husband and I are spending October 10-14th in Portland this year. We've done this trip ( as far as dates a few years in a row now , as it's our anniversary). Just looking for a few options for day trips.
We've both done Boston several times and will skip it this trip. Last year we drove to Amherst to see Emily Dickinson's home and museum, the Yankee Candle factory, Eric Carle Museum etc. That was a nice day. We like nice drives, cute little towns with good food etc.

We'll fly into Portland from Little Rock Wednesday the 10th. We'll get there around noon, and rent a car. We are staying in Freeport, and will hang out in Portland and Freeport on the 10th. We've found some cute little restaurants and shopping we like.

What should we do on Thursday, Friday and Saturday?Here are some of my thoughts but I'm open to others.
Drive through New Hampshire and the Kancamangus Scenic Hwy.
Drive down to Plymouth to see Plymouth Rock, replica of the Mayflower etc.
Drive to Bar Harbor and Acadia for the day- it's a 3 hour drive each way but we like driving and are okay with getting up early and getting back late.
Drive across Vermont to see the colors, cute little towns, maybe apple or maple syrup type places?

Again- we don't mind driving and enjoy off the beaten path.

I would vote for Bar Harbor but not as a day trip. At least spend one night up there to explore Acadia National Park. It is way to long to go for a day and you will have no time to explore on the way up or back. The Maine coast is beautiful. New Hampshire is also a great option as it will be peak foliage season then. Be sure to book where you are going to stay early as New England fills up during foliage season.

I agree Bar Harbor (although Acadia is one of our favorite places in the world) is a long way for a day trip from Freeport. Plymouth Rock longer. And Vermont's best spots even longer. We like to drive as well, but perhaps a ride to midcoast Maine including the location of our former inn (Camden) would be preferable. Camden and Rockland, and the many towns in between, would provide a good coastal diversion. That week is usually past peak for fall foliage in the mountains (places like Kancamagus Highway), but, as you probably know, the colors come later on the coast.

Do NOT drive to Plymouth to see the rock. The Mayflower is going through a major restoration at Mystic Seaport in Connecticut in preparation for the 400 th anniversary in 2020. The drive to Mystic would probably be 4 hours each way if you miss the traffic hours through Boston and Providence, although the Seaport is a very interesting look at maritime life in the 1800s.

You might visit Bath Iron Works museum in Bath, ME, the Joshua Lawrence Chamberlin Home and/or Bowdoin College in Brunswick, ME, Strawberry Banke, in Portsmouth, NH, Rockport, MA etc.

I think the ride to NH via the Kanc would be very nice - probably better on thurs due to week end leaf peepers. After reaching Lincoln you could head north to Franconia and visit the Flume or take the tram up Cannon Mtn. Lovely views and very scenic area. You could return via 302.

Oh thank you! I didn't know that. We will cross that off the list then to do. I do love colleges and will check out the suggestions you have given. Thank you!

Great! Thanks for the suggestion on route. Looks good!

The Bath/Brunswick area is a great suggestion. We also like Rockport ME which has the Farnsworth Art Museum and the Owls Head Transportation Museum. East of Brunswick is the Harpswells area which is fun to explore in the summer. I would check on restaurant hours since some might be closed after Columbus Day weekend. You can get a list of conservation areas where you can hike. Some are easy and fun like Giant Stairs.

If you decide to go to Portsmouth NH, we have enjoyed the boat cruises both harbor and inland rivers. For driving fun, starting from Prescott Park/Strawbery Banke area, drive out Rt 1B thru the charming little town of New Castle. You will also go by the fabulously renovated Wentworth By the Sea hotel. After that drive Rt 1A along the coast past grand summer mansions in Rye. Our favorite seafood shack is Petey's in Rye and it's open all year. It's fun to visit the shops in Porstmouth's Market Square area.