There is good lobster all along the coast. If you want to go into the water, wait til August and pick a nice beach south of Portland.

If you want to hike a bit too and see the iconic rocky coast, go up to Acadia.

There are plenty of ways to get there, but you will have to get by NYC and through CT,MA and NH. If 95 is behaving itself in CT, you could take it to 91 to 84 to the Mass Pike to 495 to 95,

If you don't like 95 in CT you could take the Garden State to the road that goes to Tappan Zee Bridge and follow the signs to 84 and on

That's a good advice)))

Or, once you get to Hartford I84, you can continue to head north to I91 up to VT. Get off in Brattleboro (might be exit 3) and head to Keene. From Keene you can either go Rt 101 thru the lovely Monadnock area (Peterborough might be a nice place to stop for lunch), then Everett Turnpike north to Rt 101 to I95N. Or from Keene, head to Concord NH - just about all country side. Connect with I89, then I93N to I393 east to Rt 4 to Portsmouth. This is the prettiest approach to Portsmouth since you go over the bridges over Great Bay. Easy connect to I95N.
Did I mention I hate the Mass Pike and 495? Depends on whether you want fast or pretty. Western MA is just about all farmland. Soothing.

Probably it's best to google best lobster roll because there has been some good articles with photos. We tend to wander around switching off between steamed lobster and lobster rolls and maybe a fried clam dinner once. We stay on I95 until we get to Brunswick because we like to stay in the mid-coast area. Wiscasset has been a good central location. We stayed in Bath last summer because we wanted to see their great 4th of July parade and had the benefit bbq dinner one evening. From this area you can do easy day trips to:
1. Waterman's Lobster - our favorite. It's near Owls Head Light and Transportation Museum. We just happened to find it on one trip back when they just had about 6 picnic tables. Now they have a covered porch in back and a porch in front but still have some picnic tables by the water (remember to wear a hat and sunglasses). The view is open, beautiful ocean. But it's a rustic, seasonal place with porta potties so don't expect a wine list.
2. You can spend a whole day driving around the Harpswells. Get a map for the public conservation areas for a little hiking. We liked Holbrook's Wharf last summer. Dolphin Marina is a real restaurant and so is Estes. If there's a crowd, we skip the place. http://harpswellmaine.org/restaurants/
3. But as you head out of Brunswick there's Cameron's which is mostly take-out but has a few tables and just outside of the downtown Brunswick area there's what used to be an A&W drivein that had a really good lobster roll.
4. Another good day trip is out to Pemaquid Point where you can enjoy sitting in the shade by the light house. Come to think of it, we didn't go to the lobster shacks in that area so can't give recent testimony.
5. In Wiscasset, we've never gone to Red's and we prefer to avoid Boothbay (it's just too many people and higher prices). We've had some good meals at the Sea Basket except for the last visit. This is a real restaurant but family style with a counter to place your order, no waitstaff. I think we hit a day when the teenagers weren't paying attention to cooking.
6. Last summer in Bath we also discovered the food truck where I enjoyed a good crabmeat roll with avocado. DH had fried clams. Sorry, can't remember the name. The important thing is to visit some place you might skip. Bring picnic stuff with you so you can get good stuff and maybe some fresh berries and vanilla yogurt for lunch and have a picnic. We take bag chairs in the car. There's a sweet little beach in the Harpswell area that is open to the public if you know where it is but the road in is so bad you need good clearance on your vehicle. It's on the conservation map. There's also an easy to find little beach where you can sit by the water and hardly see anyone swimming mid-week but watch some boats working.
Also get yourself a map to the wineries, a schedule of farmers markets, best ice cream places, breweries, etc. If you stay in a place with a kitchenette, you will be all set. We tend to explore and have lunch out. Then eat locally for supper. In the past we've camped alot so just cooked dinner at th campground.

The "best way?" Fly to Portland and rent a car!

We drove along the coast of Maine stopping at several different towns, staying in Bed & Breakfast Inns and "pigged out" on lobster for the entire trip. Almost every town has several "lobster shacks" to choose from - if you are a lobster lover- you won't go hungry in Maine.

It would help give you better advice if you told us when you plan to go to Maine, for how long, and how you picture spending your days. Do you want to do outdoorsy stuff like hiking and kayaking?

~Liz

I plan on going in late June for a long weekend. Don't want o go in the water just like the atmosphere.

I like the idea of driving the coast and seeing multiple towns but here to begin?

I second dfrostnh's advice. The midcoast is wonderful, with far less tourists than the area south of Portland. We love the Harpswells, Bailey's/Ors Island, and, a little farther north, Bath/Popham and Wiscasset/Georgetown. You can go farther north along the coast and see more beautiful places, but midcoast will bring you great Maine atmosphere and lower prices.

I would recommend Stonington on Deer Isle. This is a real lobster village, not a tourist town. You can take a kayak tour or the ferry to Isle Au Haut - part of the Acadia National Park. There is a great bed and breakfast, inn on the Harbor.

If you do a long weekend in mid-June the lupines would be blooming. The Stonington area has a festival. It's a small town kind of thing but you can get a map to where the best blooms are.

For a long weekend you probably want to pick a spot and stay there, maybe a day drive or two from your home base. Kennebunkport or Cape Porpoie would be nice with a day drive to Sebago Lakes. Camden/Rockland is a longer drive into Maine, nearby visit Mt. Battie or take a drive around the lakes.

Consider this little place, not a bad drive too far up into the state, and just the atmosphere you are looking for with a lobster wharf in walking distance. Nice easy drive to Kennebunkport or Sebago Lakes or Old Orchard Beach.
www.capeporpoisemotel.com

book soon because the place is small and books up fast. Note there is a $25 fee if you cancel.