Boston-Maine October Vacation Recommendations

Questions & Recommendations

Hi there! My boyfriend and I are taking a trip to New England September 30-October 8. We've never been in the area before and would love any recommendations for activities, things to see, day trip destinations nearby, places to eat, etc.

We fly in/out of Boston and plan to spend half of our time in that area and the other half in Portland, Maine. We have a hotel booked for Portland, but any suggestions for an affordable Boston hotel in a relative location would be much appreciated.

A few things we have planned already to give you an idea of what we enjoy:

We will be visiting Salem October 1—I know what you're thinking, but I promise I'm prepared to have patience, wait in line, be in crowds, etc. As a spooky lover, I just have to see it once!

In Portland we have booked a Fall Foliage Spain in Maine Chef Series Wine + Food Sail and an oyster farm tour!

We love quality museums, history, botanical gardens, beautiful scenery, walks/hikes, and most of all—SEAFOOD!

Thanks in advance for your suggestions(:

Posted Aug 7, 2025, 4:41 PM UTC

312
Loading comments…