Freeport / Portland

Portland and Freeport have become a recognized region for Maine coastal visitors seeking seaside and foodie fun. For many first-time visitors, Freeport is introduced as the “home of LL Bean” but it doesn’t take long realize the town is way more than its 24-hour shopping.  While LL Bean is Maine’s most popular attraction, the allure of Freeport and neighboring Portland goes well beyond boots and camping gear.  Like its neighboring coastal communities, the history here starts with ship building, and continues today with plenty of ocean-and-bay oriented recreation. Freeport, located on the Casco Bay, is just 20 minutes north of Portland and both are perfect stops on the Maine Coast to enjoy so much of Maine’s beauty, recreation and gastronomic delights.  Most of those who fly into Southern Maine come by way of the Portland International Jetport.  Yet Amtrak also offers the Downeaster train into Portland, and soon into Freeport too.  This is one part of New England that is well-known for its foodie delights.  In fact, Portland has amassed quite a list of food and lifestyle awards, including the best city to live and the one of America’s coolest cities not to mention one of America’s “foodiest” towns.  Take a Maine Foodie Tour, which originated in Portland and has now expanded to include Kennebunkport, Rockland and Bar Harbor, or board the Maine Brew Bus for a gastronomic drinking and tasting day trip around Portland. Then head up to Freeport, hitting the outlets and not-to-be-missed obligatory photo op at the LL Bean “big boot”. Explore Freeport’s restaurants, from the Harraseeket Lunch and Lobster Co. – your quintessential BYOB lobster shack on the shores of South Freeport – to fine dining at many of Freeport and nearby Portland’s renowned restaurants.  

Freeport’s History

Wolfe Neck Park, Freeport

Wolfe Neck Park, Freeport

Freeport is often credited as the birthplace of the state of Maine where meetings were held leading up the state’s separation from Massachusetts in 1820 in the Jameson Tavern, still standing in downtown Freeport.  Given the region’s large quantities of timber, the main enterprise in this region was shipbuilding. Yet, grist and saw mills plus fishing, canning and farming were also popular in the early days both here in Freeport and in Portland. With the arrival of the railroad in 1849 came increased commercial trade in the center of Freeport

In 1912, Leon Leonwood Bean opened a store in the basement of his brother’s apparel store and sold his iconic “bean boot” originally called the Maine Hunting Shoe.  With a commitment that continues today, LL Bean’s store was always open.  Today, shoppers can visit the famous LL Bean store 24/7/365.

Today Freeport holds great appeal for travelers across the country and around the globe thanks to its proximity to both land and sea attractions.  Many stop in Freeport as a waypoint as they travel Maine’s coastline but even more appreciate the plethora of options all enjoyed within a day’s travel.

Similarly, Portland started as a fishing and trading village, originally called Casco and then later re-named Falmouth, after Falmouth, England. In 1786, the citizens of Falmouth formed a separate town in Falmouth Neck and named it Portland. In 1785 the village was bombarded by the Brits during the Revolutionary War and three-quarters of the village burned to the ground.  When it was rebuilt, the village shifted from its former location to where the Old Port still stands today. During World War II, Casco Bay became home to many destroyers and headquarters for the Portland sections of the naval local defense force and inshore patrol. The building of the Maine Mall had an impact on Portland’s downtown during the 70’s, but today Portland’s Old Port is once again the center of the dining, shopping and seaport activity. With an emphasis on preservation, much of Portland’s Victorian architecture has been restored in the rebuilding and renovating process. In 1982, the area was entered on the National Register of Historic Places. In many lifestyle surveys, it is often cited as one of America's best small cities to live, eat and play in.

Gastronomic attractions in Portland and Freeport

Azure Cafe, Freeport - Photo courtesy of FreeportUSA

Azure Cafe, Freeport - Photo courtesy of FreeportUSA

Exploring Portland and Freeport has taken on new dimension in the last ten years as the dining and shopping scene in the Old Port have exploded.  Visitors continue to seek out the best lobster roll and a tasty brew, but now that search has expanded to enjoy James Beard Award winning cuisine, artisanal beer and spirits or the chance to partake in a cooking class to better savor it all.  

Portland’s foodie scene has exploded with talented chefs claiming residency and garnering accolades nationwide; restaurants like Street & Co., Hugo’s, Eventide Oyster Co,  Central Provisions and Duck Fat are not to be missed.  And just north in neighboring Brunswick, diners delight in chef Cara Stadler’s “perfect bites” at Tao Yuan.

Freeport’s proximity means guests can enjoy all the city has to offer and return to the quiet and slower pace of this small hamlet.  Freeport’s own cuisine options ensure a delicious and satisfying meal within walking distance of downtown inns like Azure, Tuscan Bistro & the Jamestown Tavern.

Maine’s homegrown brewers took the national stage this year with awards from magazines like Beer Advocate. Indeed Maine Craft brewers are continuing their upward momentum, having made a $227.95 million economic impact to Maine according to Maine Biz Magazine.  A journey to Portland and Freeport region offers the chance to experience exclusive pours from the likes of Maine Beer Company, Bissell Brothers, Allagash Brewing Company, Shipyard Brewing Co, Foundation Brewing along with Cold River Vodka Distilling located in Freeport and Maine Craft Distilleries offering small batch spirits.  Many of these offer tasting rooms allowing the chance to drink your way around Freeport and Portland on a tasty tour.

Retail Therapy in Portland and Freeport

Downtown Freeport

Downtown Freeport

If you ever find yourself wide awake at 3am and yearning to buy a tent, head to Freeport.   LL Bean’s famous customer service is overshadowed only by its 24 hour – 7 day a week hours.  The LL Bean flagship store never closes, and doesn't even have locks on the doors!  Along with the king of outdoor adventure clothing and gear, intrepid shoppers will enjoy over 200 name brand outlet stores like Talbots, Bass, North Face, Tommy Hilfiger, Brooks Brothers and more, along with specialty goods from Georgetown Pottery, Thomas Moser, and Chilton Furniture – both manufacturer of fine furniture,  and Wilbur’s of Maine Chocolate Confections.  Plus, a local favorite, Bessie’s Farm Goods is a short drive to find great handmade gifts, delicious treats and a great knitting circle every Wednesday!

In the late spring, summer and fall, Portland offers its signature farmers markets midweek at Monument Square and on Saturdays at Deering Oaks Park.  Additionally, throughout Portland, Falmouth, Yarmouth, Freeport and Brunswick, Farmers Markets offer up the freshest of fare from local Maine farms nearly every day of the week.  Click here for a day-by-day list of where Farmers Markets are found throughout Maine.

Portland’s Old Port and downtown area offers a collection of independently owned boutiques and shops.  Look for everything from handmade gifts and foods to apparel, housewares and more in the eclectic stores within the Old Port.  In nearby South Portland, the Maine Mall offers big box stores from Macy’s to JC Penny and plenty of smaller, popular stores too.  

Outdoor Excursions in Portland and Freeport

Reid State Park, Georgetown

Reid State Park, Georgetown

Why is Freeport’s outdoor recreation so fun to explore?  Maybe it’s the injection of the LL Bean spirit (“there’s no bad weather, just bad gear”) or maybe it’s inspired by the natural beauty. Travelers to Freeport and Portland are treated to a wide range of active adventures year-round.  

Attractions like Wolf’s Neck State Park, Bradbury Mountain, Pineland Farms, Winslow Park and Deering Oaks Park keep visitors engaged in myriad pursuits:  hiking, boating, bicycling, kayaking & SUP rentals plus swimming & golf in the warmer months.  While XC skiing, snowshoeing and fat tire bike riding rentals keep athletes warm in the colder temps.

In Portland, board a historic schooner or a guided nature cruise and explore Casco Bay and its myriad of islands.  You can also grab bicycles and board the Casco Bay Lines ferry for a day of biking around Peak’s Island, Cliff Island, Long Island, Great Diamond and Chebeague Island. Take the Mail Boat and tour all of the islands where the Casco Bay ferry goes.  You can even board the Lucky Catch Cruise, and learn about the love and lore of lobsters with a real Maine lobsterman.

For travelers seeing some guidance or instruction, not to mention fun adventure in the woods or on the water, the LL Bean Outdoor Discovery School offers year round classes and instruction on everything from survival camping, kayaking, fly fishing, to skeet shooting and lots more.  

Guests that are keen to expand their travel radius a bit will find picturesque beaches from Higgins Beach, Crescent Beach and Scarborough Beach south of Portland to Reid State Park and Popham Beach to the north and east.   


A visit to Maine is not complete without a visit to at least one of the hundreds of lighthouses that dot the coastline.   Make a day trip of exploring Portland and Freeport’s lighthouses which would include a trip to Cape Elizabeth’s Two Lights State Park to see the two side by side lighthouses, and enjoy some seafood amidst the rock cliffs at the Lobster Shack at Two Lights.  Then head to Fort Williams Park, also in Cape Elizabeth, to see the famous Portland Head Light, commissioned by George Washington and serving as a beacon for sailors and yachtsmen entering Portland Harbor. In Portland, visit Bug Light Park and you’ll see the small Bug Light lighthouse that guides ships into Portland Harbor. Venture through the Southern Maine Community College to Spring Point Ledge Light.  Here you can walk out on the granite breakwater to get close to the lighthouse and watch boats sailing by or admire it from the beach. Guests are also encouraged to see these beauties by sea aboard the ferries or regular private charters scheduled throughout the spring, summer and fall.  Or better yet, join the 5 Lighthouse Bike Tour and see Portland’s lighthouses from the seat of a bike with a guide.

Festivals & Events in Portland and Freeport

While many people think of visiting Maine in the summer, more and more guests find the winter, fall and spring just as enjoyable given the lighter traffic on the roads, less congested sightseeing and availability of a table at the most sought after restaurants.  

In Portland and Freeport regional fairs, sporting events and uniquely Maine festivals offer more than a standard weekend away, they become yearly traditions to enjoy with the whole family.  

Throughout the summer, LL Bean offers its Free Concert Series, offering up everything from bluegrass to rock and roll.  Many of the performers are well known names, so it’s always good to stake out your seat early. On July 4th, they add a huge firework display too.  Bring your own chair or sit on the grassy knoll between the Home Store and the Flagship store.  

Another summer tradition is the Yarmouth Clam Festival, held in mid -July.  The quiet town of Yarmouth, Maine – between Portland and Freeport – swells to 100,000 people as the Carnival comes to town, joined by more than 100 artisans and crafters selling unique gifts and foods and the food booths spilling over with every kind of clam treat you can imagine.  Don’t like clams? There’s a wide array of additional options, including the Clam Fest’s signature Lime Rickey.  This 4-day event includes a parade, a clam shucking contest, plenty of live music and more.

In the fall the Cumberland Fair, and Common Ground Country Fair are perfect reasons to visit Maine. Venture a little further into Western Maine for Maine’s Blue Ribbon Fair, the Fryeburg Fair.   From apple cider pressing to ox and tractor pulls, harness racing to 4H livestock competitions, these rural shows remind travelers that farm life is alive and well across our nation.  

Also in October, foodies flock to Portland’s waterfront for the multi-day Harvest on the Harbor Food and Wine Festival,  offering days of workshops, tastings and cooking competitions, all of which can be enjoyed by ticket holders.  

Sparkle Weekend, Freeport - Photo courtesy of FreeportUSA

Sparkle Weekend, Freeport - Photo courtesy of FreeportUSA

Freeport puts its best, shiny foot forward every year to celebrate the Christmas season with Sparkle Weekend.  The Fall Festival welcomes autumn while the first weekend in December is marked by parade with lighted “sparkle” floats down Main Street and Santa as grand marshal.  The LL Bean store delights young and old with its Northern Lights spectacle, live reindeer and a giant snow globe for the family greeting card photo.  But shopping is not the only attraction to the area,  Winter time offers Trail Monster Running’s snowshoe races like the Bradbury Blizzard, the annual Girlfriends weekend of spa, knitting and spinning, and the Flavors of Freeport to name a few.

Maine Maple Sunday is celebrated annually on the fourth Sunday in March and is a favorite spring holiday. Most sugarhouses offer free maple syrup samples and demonstrations on how pure Maine maple syrup is made. Many farms offer games, activities, treats, sugarbush tours, music, and so much more.  Each one is a little different but they’re all as sweet as can be!