This is East Coast Portland not West Coast Portland
Let’s Start With How You Will Get There
Fly into Boston first because it’s only 2 ½ hours to Portland
You can fly into the Portland International Jetport but it has its limitations. It finally got over 2 million passengers in 2019 so that should give you an idea of its traffic size. There is only 1 international flight. Your best bet is to fly into Boston Logan International in Massachusetts as there are numerous flights to choose (allowing you to search for the best fare for your dates) as well as giving you a quick side-trip to Boston for fun. That’s what I did recently on a trip to the WITS conference being held in Portland, Maine.
1. See Boston. Visit the Tea Party Museum. Eat at a Bakery.
I had 36 hours in Boston. What to do? Why not take an Old Town Trolley tour first! Helps to get a feel for the layout of downtown Boston and takes 2 hours if you don’t get off at any stop. And it covers all the stops you need to see for a first-time visit or even if returning. That’s what I did even though the weather wasn’t so great being overcast, cold, and drizzly. But I did make it a point to do the Boston Tea Party tour which was fun. Even got to participate in a re-creation of the town meeting harking back to the 1700’s. In the short amount of time I had in Boston I managed to also squeeze in a visit to a local bakery to get a box of goodies including the famed Cannelloni. Much better than a Dunkin’ Donut. Our tour guide made a joke about how Bostonians give directions; “Its 3 dunks straight and 2 to the right” in reference to how many Dunkin’ Donut shops are located in Boston. I used Yelp to find a bakery instead near my hotel which was the newly renovated Courtyard Marriott by the TD Garden Arena. I chose that Hotel because it is literally across from the North Train Station which offers the Downeaster Amtrak train service directly to Portland. The other stations do not. There were also several nice restaurants & pubs within 10 minutes or less walking distance. I even had a drink at the oldest pub in America which is located right by the Holocaust Memorial.
2. Travel by train on the Downeaster service via Amtrak. See the coast.
The Amtrak service was pleasant. It was early in the morning when I boarded so I planned on sleeping but instead ventured over to the Café Car for Coffee and an English-Muffin breakfast sandwich. I had a window seat to watch the countryside and coast as we smoothly sailed along. In no time at all we were at the Portland Train Station where it was easy to get an Uber/Lyft ride to our Hotel.
3. Stay Centrally Located By The Bay
Downtown Portland is easy to navigate and was only 10 minutes to the center to the Holiday Inn By-the-Bay where the conference was being held. The hotel itself is a bit on the 1980’s but it was adequate and actually large enough to hold 500 WITS attendees. Plus it has a restaurant and full-service bar with friendly staff. Registration staff were friendly and helpful too plus there is a free shuttle to take you around town. My room was on the 8th floor facing the huge Casco Bay so on the days the sun came out there was a pretty view.
4. Stay at the swank Portland Harbor Hotel
If you want to stay somewhere more upscale with a lot more amenities, try the Portland Harbor Hotel. A group of us WITS attendees in the 55+ range were given a private tour and presentation by the very friendly and accommodating staff. Sipping our Prosecco’s we were given a short presentation on a new property they are building called The Inn at Diamond Cove. It’s very luxe. We also were shown a standard room at the hotel.
5. Eat a Holy Donut not blessed by the Pope
Notwithstanding the ubiquitous Dunkin’ Donuts, we were advised by locals to try the Holy Donut. It’s a “must-try” I have to pass along to you, dear reader, as it was delicious! I had one of their popular donuts, Dark Chocolate with Sea-Salt Caramel and their signature coffee, a Cocoa Coconut flavor. On a mildly-cool weather day it was a good pick-me-up as I walked around downtown to explore the sights.
6. Walk everywhere because it’s easy to do
I started on Commercial Street and headed towards the Eastern Promenade passing historical Fort Allen Park to the East End Beach where several dogs were playing and having a good time. A few weddings seemed to be taking place in the park so I sat down on a bench to rest at Munjoy Hill and gaze at the beautiful expansive view of the harbor. This green park on a hill connects to Congress Street which has a lot of great little eateries as well as the famed Portland Observatory.
7. Eat Lotsa Lobsta
After all that walking in the brisk air, stop for a lobster meal somewhere. I ended up at the Portland Lobster Company which is rated tops in Yelp. You really can’t go wrong with a Lobster Roll either. Eat to your hearts content. They never run out of Lobster in New England.
The WITS opening night party was held at The Grace, an 1859 church that was renovated and turned into a Restaurant/Wedding Venue. We heard some good music and mingled under the purple lights. See images below.
"The Portland City Clerk's office has 536 registered food service establishments with food preparation, according to Alexandra Murphy, assistant city clerk. Assuming a Portland population of 63,000, we come up with one restaurant for every 118 people. Pretty good!"
8. Drink Liquor by way of a Maine Brew Bus tour
Now you don’t drink while someone is driving. They drive you to distilleries to sample the alcohol. Seriously, this is a fantastic way to tour Portland, Maine and meet a lot of nice people while learning about the local beer breweries, honey mead winery, and gin distillery. All in a bright green bus with a knowledgeable guide (ours was named Don) and just a whole lot of fun! Check out the schedules of the Maine Brew Bus
9. Visit an old Historical Lighthouse via a Trolley Bus tour
An easy way to get around Portland besides walking, is by taking a Trolley Bus tour which will get outside the city limits a bit to see The Port Headland Lighthouse at Cape Elizabeth. We walked 5 minutes from our hotel to the Old Port Harbor area to get on the 90 minute trolley tour. Along the way you will get familiarized with areas in the city such as the Victoria district of Greater Portland where some of these preserved Mansions offers interior glimpses. We also were told of modern celebrities born in Portland like Judd Nelson, Anna Kendrick, Liv Tyler as well as Novelist Stephen King. Then there are important historical poets like Henry Wadsworth Longfellow.
10. Take a ferry boat ride to one of the Calendar Islands
Casco Bay in Portland, Maine has over 300 small islands called the Calendar Islands. I had a daytrip via ferry out to Cow Island (which is part of Long Island) with several other WITS attendee’s courtesy of Rippleffectmaine.org. Rippleffect is an organization that creates outdoor youth activity camps & getaways for public schools in the Maine area. Cow Island has a zipline and rock climbing wall as well as numerous other activities designed for bonding experiences. It’s quiet and isolated. I saw 2 Peregrine falcons flying overhead as the only other life that was inhabiting this quaint nature island. The other islands offer many hike & bike opportunities as well as places to stay & eat.
11. Car ride to Freeport visit the 24-hour LLBean store
One of the attendees I met at WITS is a travel advisor like myself, named Nancy Dorrans who runs Adventure Marketplace. As a local, she welcomed the WITS attendees and soon was making friends with many of us by taking us around to show us the sites, all impromptu and in her car. We had a fun time going up Interstate 95 in about 20 minutes to Freeport where L.L.Bean’s Flagship 24-hour store is located. Instead of shopping, however, we dropped one of our group members off at the beautiful Kendall Tavern Inn Bed and Breakfast where we were given an impromptu tour of a very nice place to stay if you’re ever in the area. Afterwards we had dinner at the historic Jameson Tavern (built in 1779) for more Lobster and drinks.
Note: Should you have access to a car and want to take a longer ride up north, check out this post on traveling from New York to Acadia National Park Road Trip which takes about 9 hours. It's an option to consider if you fly into New York instead of Boston and rent a car.
Otherwise if you're already in Portland it's only a 3 hour drive to get to Bar Harbor, Maine which is right next to Acadia National Park.
Something for Everyone No Matter How Short of a Stay
There are many more things to see and do in Portland, Maine. I’ve only listed the things I personally did on a weekend in May 2019.
If you are really short on time maybe only have a day to do something check out what you can do in under three hours.
In any case, and for any length of time, you can always find something great to do, somewhere nice to stay, and something delicious to eat, in Portland, Maine!