This quaint New England seaside city has converted numerous pre-war maritime warehouses to art galleries, restaurants and bars. This among many other New England state capitals brings a thriving restaurant scene to walkable historic cities that are easily manageable on a weekend. This is a great long weekend from Boston, MA, and is only a two hour drive.
For those interested in literature I would recommend reading Olive Kitteridge by Elizabeth Strout, Empire Falls by Richard Russo, or Maine by Courtney Sullivan, all of which are set in Maine.
Arrive and get settled in your hotel. I stayed at Courtyard Portland Downtown/Waterfront (321 Commercial St, Portland, ME 04101) which was an easy location to walk to everything downtown.
Get some grub at Fore Street (288 Fore St, Portland, ME 04101) then enjoy a rooftop drink at Top of the East (157 High St, Portland, ME 04101) on the top of the Westin Hotel to get oriented on with the city and if possible watch the sunset.
Start your morning off with breakfast at LB Kitchen (249 Congress St), you order at the counter and get the food served to your table.
Portland is great for a seaside bike ride. We rented bikes from Portland Encyclopedia ( 6 Commercial St). On your ride don’t miss both Bug Light and Portland Head Lighthouse (12 Captain Sprout Cir, Cape Elizabeth, ME 04107) Take a break and grab a lobster roll from the Bite of Maine food truck, right outside the Portland Head Lighthouse. They will NOT disappoint!
After biking, relaxing over an IPA from Shipyard brewing company. We spent some time at the brewery. After getting your hops on, window shop down the Old Port section of the city. This is quintessentially New England with the cobblestone street and colonial brick buildings. I did not miss out on tasting Portland’s favorite donut shop, Holy Donut (7 Exchange St), which is a great afternoon snack.
Get dinner at Eventide Oyster Company (86 Middle St, Portland, ME 04101). This sleek and busy restaurant is great for any seafood lover. We ordered some oysters for the table and then continued to sample most of the menu!
Get breakfast at Tandem Coffee and bakery or the standard baking company before heading for a last walk downtown and head home.
If you are interested in other ideas for weekend getaways from Boston, check out my article 5 Seaside Getaways from Boston.