Colby College, etc, end of May
 

My husband has a business engagement at the college end of May, and I'm wondering whether there's anything great in the way of hiking, eating, exploring in the area. We don't know Maine well,but had an absolutely spectacular 9 day vacation downeast some years ago in July (Portland up to Acadia). I'm trying to decide whether to do a repeat of that earlier trip, or whether it's likely to be too cool for pleasant strolling, hiking, sightseeing in May/very early June. Perhaps the southern part of Maine? But my sense is that the southern part isn't anywhere near as handsome as farther up? Maybe head to Massachusetts coast after the Colby engagement instead?
In short, we love the ocean, beautiful trails (moderate) and great food and great inns. Will be very appreciative of knowledgeable in-put. Thanks so much.

Things just start to come alive in Maine at the end of May, but lots along the coast is still closed. Lots of summer inns & restaurants are waiting for the college kids to get out of school and are just beginning to train them for summer work.

There is a very nice lake area near Colby, Belgrade Lakes, with a nice B&B called Wings Hill Inn. More rustic and right on the lake is Alden Camps, little cottages on the lake with an excellent dining room. aldencamps.com

On the Coast, Camden and maybe Ogunquit would be the only towns that are starting to hop that early in the summer. Weather can be iffy...light rain and 65 is probably more likely, but if you're lucky you could hit some 75 and sunny days.

"Handsome"??? Why would you assume that?

May will be much, much chillier than July.

You may want to consider Kennebunkport, Ogunquit, York Harbor, for example, in Maine, Portsmouth, NH, Newburyport, Gloucester, Marblehead, Salem, just to mention a few, in MA.

Highly recommend "Maine, An Explorer's Guide" and "Massachusetts, An Explorer's Guide", for determining destinations you would find most "handsome". Fabulous resource(s) for hiking, dining, inns...

All the appealing seacost villages and towns are unique and appealing. All turns on your preferences.

I think djkbooks gave you some excellent choices and wonderful books to look at -
I have lived on MA coast all my life, and been in and out of many east coast harbors in the boat, and my son attends Colby -
I love the coast from Provincetown to Canada -
there are nooks, crannies, rocky harbors, serene open harbors, marsh areas, you name it - and hiking and walking all along-

I think it is as pretty in the southern part as the northern part - and all thru MA and the islands - the New England coast is gorgeous.

people hike in new england all year long, but it sounds like you would prefer it be warmer so based on that I would head further south, still realizing it is New England and it could be unseasonably warm or cool, damp and rainy.

It is high school and graduation time so I would make my reservations asap. - Colby graduation is May 26/27 and most parents have already booked their rooms, some as far away as an hour from campus

Perhaps if you described what "handsome" means to you, it would be easier to suggest similar areas - does handsome to you mean dark cliffs and lots of rocks, thrashing waves, etc - and you don't find handsome serene harbors, surrounded by marsh and calmer waters, less rock - bobbing lobster boats - is this not handsome to you? SO yes, some of these areas have more of one than the other, but in most areas I cna think of you could find both.

for hiking you could also look at
thetrustees.org

it is the site for the Trustees of the Reservations and will show you all the hiking, walking paths, - look at the hiking and property maps and also at the links to accomodations.

If you do the Ipswich area, the Inn at Castle Hill is lovely - (Ipswich, Marblehead, Salem, Rockport section of MA)

Lots of great info here-- for which many thanks. I'm going to start delving into some of the material and will no doubt come back with further questions.