Getaway: Massachusetts and Maine Coastal Drive + The Berkshires

The first time we drove to our place in Nova Scotia, we did it on the Trans Canada Highway and tried to get there as quickly as possible.

Never again.

After I threatened to sell the car and fly back (I can be dramatic like that), we agreed to drive back on a much more scenic route and discovered the beauty of coastal Maine and Massachusetts. We decided to take a similar route this time. I believe that the journey is every bit as important as the destination.

There were so many highlights, but here are a few standouts:

Newburyport, Massachusetts

This is a gorgeous oceanfront town about an hour from Boston with lots of terrific restaurants. We ate at the Paddle Inn and I had the Montego Bay Dinner with locally caught fish, coconut callaloo greens, pineapple jalapeño salsa, and plantain chips.

Delish! It was the end of the Yankee Homecoming festival and there was a huge fireworks display in the evening to celebrate that had the best fireworks display I’ve seen in years (they recreated a thunderstorm with fireworks!)

Freeport, Maine.

The main reason to come here is to see the L.L. Bean flagship store. I wanted to pop into the Ralph Lauren outlet since I was hoping they would have some pieces that gave their 50th anniversary a nod. I lucked out with a cardigan sweater, tennis sweater (very like RL one I had in high school!) and an oversized crest t-shirt. And everything was 112% off or what-have-you, so it was all a very good deal. I also picked up a couple of pieces at Vineyard Vines. Because whales. We ate at Linda Bean’s Maine Kitchen and Topside Tavern, which has a very capable chowder. It’s worth a stop enroute if you want to quickly hit some outlets.

St. Stephen, New Brunswick

We stopped overnight in the little town on the Canadian side of the Maine-New Brunswick border. We stayed at a sweet B&B called the Blair House Heritage Inn. The were two other couples and a singleton at breakfast and we chatted about travel and US politics over our blueberry pancakes.

York Harbor, Maine

This is a gorgeous town. This part of the Maine coast is covered in beautiful summer houses and the scenery is beautiful. The chowder at the York Harbor Inn is lovely. And the Stage Neck Inn looks like a delightful place to stay. We hugged the ocean from there back towards Boston and drove by stunning beaches in Maine, New Hampshire, and Massachusetts.


Route 1, Maine

If you have time to spend in Maine, taking Coastal Route 1 is highly recommended. There are lots of pretty towns like Camden, that are charming and filled with spots to grab a fresh lobster roll and shop for antiques. Anywhere between Newburyport and Ellsworth is beautiful. We were there for the Maine Lobster Festival so the lobster was plentiful.

Rockport, Massachusetts

I fell in love with Rockport and Cape Ann as a kid and that inspired my eventual desire for a summer place in Nova Scotia. While some are drawn to bold ocean or the beach, my love is for lobster traps and artists colonies. It was fun to go back. As a child, we stayed at the Yankee Clipper Inn in the Quarterdeck. This time we stayed at The Emerson Inn. It was lovely. They have a beautiful porch filled with rocking chairs overlooking the sea. They serve breakfast oceanside (with wild blueberry scones!)  There was a TV film crew staying there and I’m really hoping they were shooting an East Coast derivative of Southern Charm.

Bearskin Neck is a little walking village close by with cute shops and galleries. It has a bit of a Key West vibe. We ate at 7th Wave Restaurant and had the Trinidadian Curry with Gulf Shrimp as a break from the scallops and lobster. The food was decent and the views spectacular.

The whole area is antique lovers paradise. Essex is a particularly good town for antiques and you can shop at the cheap and cheerful White Elephant or the spendy (but magnificent) David Neligan, which is chock-a-block full of treasures and reminded me of the old ABC Carpet and Home before it became all hipster.


Stockbridge, Massachusetts

On our way from Boston to Toronto, we needed a stop for lunch. Stockbridge is in the heart of The Berkshires (or Berzerkshires, if you’re a RHONY fan). It’s also the heart of Norman Rockwell country so you know it’s picturesque. We ate lunch at the Red Lion Inn and it was fabulous (book ahead as it gets busy with Tanglewood audiences going to nearby Lenox.) I highly recommend the turkey sandwich (with stuffing, of course!) with a cup of chowder.

My next post will focus on dining on the south shore of Nova Scotia. Hope you are having a fun end of summer! Can you believe it’s almost September?



  1. So many good recommendations! You’ve definitely been having a great summer. 🙂 I so agree about the Trans Canada, that drive through New Brunswick would make anyone insane. I have to make note of these picks for a road trip someday, wouldn’t it be lovely in the fall too?
    Speaking of which, can’t believe we’re so near September, the summer went by incredibly fast. Hope your back to school prep is going well xxx


    • The fall is spectacular. That’s when we first fell in love with the place. And most of the restaurants are open until Canadian Thanksgiving. Plus, fewer tourists! I can’t believe it’s almost school. I’m so behind in preparation. I don’t want summer to end! XO


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