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Trip Report Three Days In Portland, Maine

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My husband and I - youthful 60-somethings - just returned from a summer trip to New England, which included two and a half days in Portland, Maine. I wasn’t sure what we could accomplish in such a short time, but we enjoyed ourselves and saw a lot. So, I thought I’d share how we spent our time.

Day One

We arrived in the mid-afternoon for a two night stay at the Inn on Carleton, a lovely B&B located on a tree-lined residential street in the West End of Portland. There are six rooms in a Victorian and the new hosts, Leo and Patti prepared nice breakfasts and couldn’t have been more helpful. From there, we walked about 20 minutes to the Old Port area and just strolled this neighborhood of shops, restaurants, bakeries and, along the water, seafood restaurants, ice cream parlors and other good, fast food. I remember this city from forty years ago when it was an old, sea-faring port with lots of old, brick buildings so common in New England. It’s now gentrified and vibrant with lots of young, enterprising residents who have opened shops, galleries and restaurants. Cobblestone streets are just blocks away from a major thoroughfare and new chain hotels dot the waterfront area. The big restaurants on the piers were overflowing with people of all ages on the Sunday we were walking around.

We enjoyed a large bucket-full of steamers at the old-timers’ favorite waterfront haunt - Jay’s Oysters. I’ve never seen such large clams. There was a crowd indoors, which looks like a dark saloon, but we chose one of the five or six tables outdoors overlooking a pier. We got a table after a short wait around 5pm, and the lines started forming right after we sat down.

We continued walking around and picked up food to go at B.Good, one of several locations in the Northeast, to enjoy later at the Inn. They make delicious and healthful food - salads, burgers, even artisanal lemonades.

By the way, If you’re on Gluten free diet, this is a good city to live in or visit as most every restaurant offers GF items and delicious GF bread. There’s the all GF bakery, Bam Bam and The Holy Donut, with a location in the port area as well as in the West End.

Day Two

The next day, we drove our rental car to explore the area beyond Portland. We drove 12 miles to Cape Elizabeth where we saw the iconic Lighthouse. A two-dollar admission fee lets you into the museum, which I highly recommend. There’s a food truck parked there that sells Lobster rolls, which we were told were excellent. But we were headed for lunch in Ogunquit.

From there we drove 34 miles (about 45 minutes) down the highway to Ogunquit. We drove through the quaint town to Perkins Cove where we had a nice lunch on the outdoor patio of Jackie’s Too. (There’s another restaurant, Oarweed, next door which serves more casual food). The view is sensational and it’s nice to be outdoors if the weather is good. Afterwards, we walked along the Marginal - a 3 mile (1.5 each way I was told) walk along the coastline, with areas for rest and taking in the view. You’ll also see some magnificent homes along the way. Definitely worth your time.

From there we headed back north, this time stopping in Kennebunkport, another quaint coastal town, famous for the Bush Family compound and, among other things, The Clam Shack. This is supposed to be the best place to get a lobster roll, but we found it to be bland and boring. Maybe it was just a bad batch. There are lots of shops and art galleries to browse and it’s lovely to walk around. If you get a map of the town, you’ll find the street where captains’ stately homes were located. (we never made it). We drove on Ocean street, which takes you out along the waterfront, gawking at the beautiful homes including the Bush’s. We also went up side streets in the residential areas admiring the white homes, with picket fences and beautiful gardens. I can see why summer is so nice here.

We headed back to Portland with the intention of taking the Casco Bay Line Ferry over to Peak’s island for dinner. But we decided instead to stroll around the port area and eat at the excellent Petite Jacqueline bistro, located in the west end near our B&B. The weather was still warm, even at 7pm, so we sat outdoors (next to a busy japanese noodle restaurant), and had casual, unfussy but sophisticated food. Highly recommend.

Day Three

We had just a half day left before catching a flight out, so we visited the Portland Museum of Art, a gem of a museum. On exhibit were the paintings (that look like large format photographs) of Richard Estes. Fabulous. If you’re in Portland before September 7, do yourself a favor and see this exhibit.

Finally, with barely an hour to spare, we headed over to Portland’s Jewish Museum. I was curious about the history of a jewish community in Maine. It’s located at the historic ETZ Chaim Synagogue on Congress Street and, if you’re so inclined, it’s worth a visit. The executive director of the museum took the time to show us around and explain its mission to honor the legacy of Maine’s jewish immigrants while bringing the diverse population of Portland together for special events like theatre and art exhibitions. Right now, there are paintings depicting the summer camp experience in Maine - I had been a camp counselor in the lake region in the 70s and it brought back a lot of memories.

I think 3 days is plenty of time to get a feel for this small, but evolving city. As for food, there are plenty of really good restaurants that would win stars in major cities. In fact, we had booked reservations way in advance at FORE, one of the city’s best restaurants, but we cancelled it when we saw how many options there were for good local seafood in more casual environments.

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