Many restaurants and good shopping. Hugo’s is a local favorite and quite fancy. The same chef, Rob Evan’s, has also opened Duckfat at 43 Middle Street; far more casual than Hugo’s with paninis, soups and salads. The Belgian fries sound good. If you like art, then ‘First Friday Art Walks’ could be fun.
Eastern Promenade Bike/Walk Path :: Great for walking or biking with great views of the working Portland harbor and surrounding islands. It holds several concerts throughout the warmer seasons; in 2012, hosted Mumford and Suns open air concert
Slightly off the path on Steven’s Ave you will find the historic Eastern Promenade Cemetery.
Novare Res :: Upscale Bar specializing in imported and local beers and a local staple. Holds several events throughout the calendar year.
Bug Light, South Portland :: A small, secluded lighthouse tucked away in South Portland across the water from the Eastern Promenade with great views of the Portland skyline and harbor
Fore Street Restaurant :: Upscale restaurant; in 2002, Fore Street was named Number 16 in Gourmet Magazine's Top Fifty Restaurants of the United States. Also visit Standard Bakery just below the restaurant for handcrafted breads and pastries
Portland Public Market :: A collection of amazing restaurants upstairs and fresh market goods downstairs
Fort Williams and Portland headlight :: Located in beautiful Cape Elizabeth- a short drive from Portland and a staple for anyone.
Shipyard Brewery :: Located just outside the historic Old Port, Shipyard brewery has a gift shop and tours available to the public daily.
Micucci’s Italian Market :: Marketplace/shopping/Restaurant
Hidden gem!!!! During lunchtime, follow the people walking to the back of the market to find freshly baked “Sicilian slab” pizza slices and breads. Be quick because they make limited batches and it goes quickly. Note- one slice will feed two people for $5.00.
Portland Green Drinks :: Similar to “First Friday” Art walk, Green Drinks is held on the second Tuesday of every month and is sponsored by local Maine non-profits. The event moves monthly so check the website to find out where the next is being held.
A big thank you to Mario Giampetruzzi for sharing his gems in Portland.
• Did you know that there is a Wine Trail in Maine? In fact, there are 20 wineries across the state. Click the link to find out more.
• You could start with some shopping at the outlets in Kittery, Maine. A shopping outlet mecka. You could definitely go here on a day trip from Boston.
• If you drive further from Boston, you will find the outlets in Freeport, Maine, home of LL Bean , open 365 days a year, 7 days a week, 24 hours a day - if you need anything outdoorsy for hiking, biking, fishing, etc, you could stop here.
• Kennbunk and Kennebunkport quaint and typical New England seaside towns. It gets really busy in the summer but it’s worth it. Lots of seafood restaurants from the small shacks to the fancier places. Plenty of shopping, and cute inns to stay at. You can stop in Kennebunkport and have delicious seafood sitting outside just by the water. There is a brewery which has good food and great beer but I would maybe suggest going for one of smaller places, just for the experience. You may think that the Kennedy’s had their estate here but it is actually the Bush family who have a summer retreat here. You can’t visit but you can see it from the road, follow Ocean Avenue, north from Kennebunkport.
• Ogonquit is another quaint seaside town. Very cute. lots of little stores, restaurants, pubs, and inns. Very popular.
• Bar Harbor If you want to go sailing (and who doesn't?), you should check out Acadia Sailing Company.
• If you are in the area of Brunswick, Maine, ‘Spindleworks’ could be a neat stop. It’s an art gallery and a store. It’s over 2 hours northeast of Boston. May not be open weekends so check the website first or call them at 207 725 8820