Family Trip To Boston in October- One/Two Nights Elsewhere, but WHERE?
 

Hi! We are taking a family trip (2 adults and 3 kids, aged 10, 7, and 5) to Boston 10/18-22. After spending 2 nights in Boston, we'd like to spend our remaining 2 nights somewhere within a 2 hour drive from Boston. Being that we are traveling with young-ish kids, extensive hiking is out of the question, but we'd like to see lighthouses, possibly do a whale watching tour, see historical sites, eat lobster, and experience fall foliage. We are not into "children's museums"- we like to explore and experience new things. We have looked into Portland, ME, and Salem, MA, but I am feeling overwhelmed with trying to figure out what location will offer us the most to do with children and a quintessential "New England" experience! Any help is much appreciated!

Portland might be a good choice. You're getting to the end of the foliage season but should still be some color on the coast. Also look into Portsmouth NH. Both the harbor and inland rivers cruises are nice. Lobster is everywhere. Just south of Portsmouth in Seabrook are two paper plate/ order at the counter type places, Brown's and Markie's. Our favorite place however is small sit down restaurant, Petey's in Rye. There is also Strawbery Banke historic area. You said no children's museums but I think Odiorne Point state park and Seacoast science center is for all ages. Haven't been since chaperoning school field trip many years ago. They change to winter hours Oct 15. Odiorne includes old fort that was part of defense system during WW2. The harbor cruise would include view of old Navy prison and Portsmouth Naval Shipyard which is actually in Kittery ME. Plenty of activity choices in the area.

If you didn't want to drive in and around Boston, look into taking an Amtrak Downeaster train from Boston North station. The flagship store of L.L. Bean is in Freeport ME and is within walking distance of the train station.

May be too late in the season but we once did an outstanding whale watch from Gloucester which is on Cape Ann and easy to get to from Boston, either by train or car. If you did want to explore other places such as Salem in/around Cape Ann you would need a car.

Portland has six lighthouses in the vicinity and whale watching continues through October. The Old Port with cobblestone streets lined with old buildings will give you a sense of history.

Two days is barely enough time to explore Boston and its historic sites. Stay there for all four days.

Salem is very busy all of October with Halloween and witch theme activities. Reservations might be an issue.
Either location is great and I'm sure you'll enjoy them.

Mystic Seaport, great even without kids, but especially great with kids.

I'd stay in Boston. Two days is so short for a city that size. That said, from your wish list obviously seems like you want to be along the coast somewhere? Asking because you could easily drive to western Massachusetts or southern Vermont or New Hampshire in that time frame. Very beautiful parts of the states but not coastal but mountains, lakes, streams/rivers, lookout points, etc.

If you didn't want to go as far as Mystic, try to visit the submarine museum in Groton CT. It is a great place for kids. You can take a self guided tour through the USS Nautilus which was the first nuclear powered submarine. Free admission (closed all Tuesdays and Thanksgiving,Christmas and New Years Day).