The wharf, below Congress Street in the Old Port district of Portland, Maine.

The Amtrak Downeaster Rail begins in Portland, Maine and ends in Boston, Massachusetts. In between there are stops in Old Orchard Beach ME, Saco ME, Wells ME, Dover NH, Durham NH, Exeter NH, Haverhill MA, and Woburn MA. For this series of articles I will expound upon the merits of each stop along the Downeaster Amtrak tour.

I have made absolutely no secret about my love of Portland, Maine. One of my first articles for UpTake was about the Portland Head Light. Then back in September I wrote about how I left my heart there. The fact that the Amtrak Downeaster line begins there (or ends there, depending on where you’re starting from) just adds one more point of excellence to brag about for my favorite city.

A shot of our pub crawl along Wharf St. in the Old Port.

You can’t ask for a better jumping-off point for everything you care to do in New England. The nearby CAT ferry (which I wrote about in this article) is ready to take you to Nova Scotia. There are miles and miles of coastline to explore if you’re headed in the direction of Bar Harbor. The Lakes Region is a day’s drive away. Or you can just stay in downtown Portland and enjoy all that it has to offer. Here are just a few of my favorites:

- J’s Oysters. This oyster bar serves, hands down, THE best crab legs I’ve ever had. Oh, sure, and oysters too. But the CRAB, man. The CRAB. It’s a tiny dive of a place with a raucous and cheerful staff, right on the waterfront with a back door that opens up to the docks and the boatloads of swimmingly fresh seafood. Fresh as in, like, five minutes ago they were happily minding their own business at the bottom of the sea, fresh. Trust me, you don’t want to miss this place.

- Bar hopping. Paved largely in cobblestones, partially closed off to pedestrian-only traffic, and home to much of the nightlife, is the Old Port section of Portland. Party in upscale elegance and sip complicated drinks, or hunker down at a more humble establishment and knock back a few beers. Or, do what we do, and make a pub crawl of it all. Take lots of pictures – you may not remember the details the next morning. (Here is a list of places to get you started.) One memory in particular comes to mind – you haven’t lived until you’ve celebrated Cinco de Mayo at an Irish Pub (Bull Feeney’s to be specific) with a bunch of sombrero-wearing, mustache-sporting Maineiacs.

The Portland Regency Hotel.

- Shopping, people-watching, and performance art. There are more little hole in the wall stores stuffed into the old cannery buildings and whatnot that you’ll never see them all in a day. Enjoy some high end retail items, or indulge in some well-crafted tourist kitsch. Browse art galleries and museums, and take in live shows and performances at One Longfellow Square. Portland is THE perfect city for hand-in-hand strolling.

- Convenient, comfortable, and historic lodging. The Portland Regency Hotel is hands-down my favorite place to stay, and is a mere three minute walk to the heart of the Old Port, and the waterfront itself. The handful of bed and breakfast inns along State Street, such as the Wild Iris Inn, offer quaint lodging at affordable prices. For an upscale hotel experience, choose either the Portland Harbor Hotel, the Eastland Park Hotel, or the Hilton Garden Inn. All are within walking distance to all the great entertainment and dining options that Portland has to offer.

And when you’ve had your fill of the area, simply hop on the Amtrak train and head toward your next stop on your Downeaster Adventure. More articles are coming soon!

Past articles in this series:
Amtrak Downeaster Adventure – Overview

Photo credits (all): Tiffany Joyce.