The fall foliage of Maine. Photo credit Arlene Avidan.

The East coast is beautiful in the fall. One great way to observe the seasonal changes is a road trip, where you get a chance to see the fall foliage up close and personal.  The only downside is it marks the end of warm weather and signals the winter ahead.  We were invited to our friends’ house for an insider’s weekend in Maine.  Any excuse to spend time with them and you can count on us to be there.

The Portland/Freeport area is perfect for an abundance of outdoor activities for families, great dining, and tons of shopping – think the land of LL Bean. We’re sharing some favorites of ours and of our friends, so you get the local input as well as the visitor’s.


Portland is such a cute little town right on the water with cobblestone streets.  Commercial and Middle Streets are the main areas for shopping and dining, but you can always explore the side streets for great finds.


Places to stay:

  • Portland Harbor Hotel (cozy and great location)
  • Portland Regency (higher end, older, gracious hotel)
  • Hilton Garden Inn (right on Commercial Street)
  • Marriott Residence Inn (by the ferry terminal)


  • Fore Street:  It’s consistently one of the top restaurants in the U.S. with great food and ambience.  You need advance reservations or can sit in the lounge as walk-ins.
  • Miyake:  It has the best Japanese, Sushi, Udon soup, and noodle dishes. The less pricey version is Pai Men.
  • Street and Co:  It’s very popular with great food – try the grilled fish – and service, plus reasonably priced.
  • Duckfat:  Offers a creative menu with GREAT french fries with dipping sauces.
  • Little Tap Room:  It’s one of our favorites off the beaten path, with good brews and casual, local food.
  • Porthole:  There is an outdoor bar and deck and a pub-type menu.  It offers live entertainment, $3 draft beers, is lots of fun for groups, and has a popular brunch.
  • Some fun, casual, and inexpensive places:  Flatbread Company on the wharf, Eventide Oyster Co., East End Grill, Standard Baking Co., Gelato Fiasco, and Ribolitta.

Things to do:

  • Take a jog or stroll along the Casco Bay, heading east along the jogging path.
  • Take a tour of the largest brewer in Maine, Shipyard Brewing, or hop on the Maine Brew Bus to visit multiple local microbreweries.
  • There are many free activities to do, such as hiking in Fort Williams Park – be sure to see Portland Head Light, purported to be the most photographed lighthouse in the world – visiting museums, and strolling the Old Port.
  • Be sure to check the weekend calendar, which is published every week and has all sorts of cool activities, happenings, foodie stuff, races, etc.

Freeport Area

Venture up to the land of LL Bean, where there are dozens of cool outlet shops, including Patagonia, North Face, and Horny Toad.  When you tire of shopping, you can choose an outdoor activity or grab a bite to eat.

Places to stay:

  • Brunswick, home to Bowdoin College:  We love staying at the Brunswick Inn on the village green, especially in the carriage house.  Christmas time is magical here.


    Brunswick Inn. Photo credit Arlene Avidan.

  • Freeport: The Harraseeket Inn is a large and popular Inn and is centrally located, within walking distance of LL Bean.


  • Freeport:  We like the Broad Arrow Grill in the Harraseeket Inn.  Sit outside on a chilly night by the open wood fire, even in winter!
  • South Freeport:  We love the Harraseeket Lunch and Lobster Company.  It’s a family owned favorite with the locals and has been written up in many foodie magazines.  You get fresh lobster and can even take them home.
  • Yarmouth:  Our favorite place is Gather, off Route 1.  It has really great local food, an open kitchen, a sharing table, great local brews, is very well-priced, and casual.  During the winter you can even cross-country ski there.
  • Brunswick:  There are a number of great restaurants. We like Frontier in Fort Andross just before the bridge to Bath. It’s a great local spot with an inventive bar.  For lunch, try Wild Oats for soups and sandwiches.  It’s a favorite with college students and locals.

Things to do:

  • If the weather is nice, you can partake of the many adventures and classes that LL Bean offers, such as kayaking, archery, skeet shooting, and fly casting.  You can also rent kayaks on your own at Rings in South Freeport.  They will outfit you with everything and drive you to and from the launch.
  • Hit the Crystal Spring’s Farmer’s Market in Brunswick for local, organic foods, seafood, fruits, and vegetables.
  • You can hike and mountain bike in Bradbury State Park or just take a bike ride with your friends, especially if your triathlete is in training.


    Heading out for a bike ride with friends. Photo credit Sherry Wernicke, Triathlon Traveling Mom.

  • Cross country skiing and snowshoeing in winter are great options. Snow jogging is also quite popular – go figure.  The best place to cross-country ski is Pineland Farms, which is a world-class facility and home to the U.S. biathlon team training center.  There are snowshoe trails there, too.  Pineland’s is absolutely gorgeous and on a clear day, you can see MT Washington in NH.

So, there you have it.  Many great places to stay, dine, and things to do in the Portland/Freeport, Maine area.  You will never be bored, even if you choose to do nothing but look at the gorgeous foliage or sit by that roaring fire…