Six Amazing Day Trips: Maine

The northernmost state in New England, Maine boasts almost 230 miles of coastline dotted with picturesque lighthouses, fishing villages, and thousands of islands. During the summer months, there is no better place to take a road trip; the drive covers hundreds of scenic miles to explore before reaching the amazing views from Cadillac Mountain in Acadia National Park. The interior of Maine is a wilderness filled with thousands of lakes and rivers nestled among immense pine forests. During the winter months, ski enthusiasts are attracted to the many world-class ski resorts. Our day trips from Portland explore the charming seaside towns, local shopping scenes, award-winning restaurants, and unique points of interest and activities.

Here are six great day trip destinations across the Pine Tree State:

Bailey Island in Harpswell (Small Town Experience)

After a short one-hour drive northwest from Portland to Brunswick and then south on Route 24, you reach the charming fishing village of Harpswell. With only 400 year-round residents, Bailey Island is one of three area islands, including Sebascodegan Island and Orr’s Island, all connected by bridges. Spend the day sightseeing and exploring the beaches, coves and trails. A few of the must-see points of interest are the Bailey Island Cribstone Bridge, Land’s End Beach, Mackerel Cove, and Giant’s Stairs & McIntosh Lot Preserve. Have lunch at one the local seafood restaurants with amazing views of the water— you’ll probably pass Cook’s Lobster & Ale House, Morse’s Cribstone Grill, and Giant Stairs Seafood Grille on your adventure around the island. Bailey Island is also reachable using the seasonal Casco Bay Line Ferry Service. The day cruise excursion to Bailey Island is about six hours round trip and allows you to disembark for two hours on the island. Leave the driving to the captain and learn about the history of Casco Bay’s lighthouses, historic sites, and summer colonies on this unforgettable day trip.

Boothbay Harbor (Museums & Attractions)

The quintessential seaside town of Boothbay Harbor is located just 60 miles northeast of Portland and is a must-see destination on any coastal summer trip in Maine. The expansive downtown area covers multiple streets with galleries that represent the high-quality local artists, unique gift shops, and an excellent culinary scene. This day trip explores a few of the local museums and points of interest. The Coastal Maine Botanical Garden is the largest botanical garden in New England. The gardens encompass 295 acres, 17 of which are gardens showcasing native plants suited to northern coastal areas. Another local gem is the Boothbay Railway Village, a preserved and re-created village consisting of vintage buildings around a village green. The museum also maintains and operates a fleet of steam and diesel locomotives on over three-quarters of a mile of track. The collection has been carefully curated and is a great representation of historical New England.

Camden (Tours & Experiences)

The Midcoast Maine summer vacation colony of Camden sits on Penobscot Bay just 80 miles northeast of Portland. The local population more than doubles during the summer months with an influx of visitors arriving to enjoy one of the most beautiful small towns in the United States. Spend the day strolling along the seaside downtown area, which includes locally owned boutiques, antique shops, bookstores, gift shops, and art galleries. Enjoy lunch at one of the seafood restaurants along the beautiful Camden waterfront. A highlight of this day trip is sure to be a day sail on the Schooner Olad departing daily from Camden harbor. The passenger sizes are small and perfect for seeing the hidden mansions, rocky islands, lighthouses, and wildlife while relaxing on a spectacular sailing ship. 

Kennebunkport (Tours & Experiences) 

Kennebunkport is a former fishing village with roots in shipbuilding and maritime activities, located about 30 miles south of Portland. Today, the resort town attracts visitors to the charming downtown area centered around Dock Square. Spend the first half of your day on the water on an unforgettable excursion with scenic views of the local coastline. Choose from sightseeing cruises, fishing trips, or, if you are looking for unique, a Lobster Boat Tour from Nonantum Resort Marina. Board the 1963 oak-planked lobster boat for a one to one-and-a-half-hour tour of the Kennebunk River and the beautiful Kennebunk coastline with Rugosa Lobster Tours. After the tour, return to Dock Square and enjoy the rest of the day visiting the boutique stores, art galleries, coffee shops, and local restaurants. There’s no shortage of fresh seafood, delicious ice cream, or, the official State Treat of Maine, a whoopie pie.  

Rockland (Small Town Experiences)

Nicknamed the “Lobster Capital of the World”, Rockland is located along the coast, 80 miles northeast of Portland. The small town has plenty of things to do with worthy museums, art galleries, and boutique shops. This day trip combines explores the heritage and culinary scene with two things that are often associated with Maine: Lighthouses and Lobsters. The Maine Lighthouse Museum is home to the largest collection of lighthouse, life­saving, and U.S. Coast Guard artifacts in the nation. For the foodie seeking local seafood, Rockland has dozens of restaurants across town, ranging from casual to fine dining. We recommend exploring the menu at Claws for a wonderful view of the downtown harbor. The award-winning restaurant serves only the freshest seafood available sourced from local fishermen. You really can’t go wrong with the lobster roll!!

Naples (Parks and Recreation) 

Referred to locally as “The Lake”, Sebago Lake is the second largest in Maine and the deepest in New England. It’s located about 30 miles northwest or Portland and is estimated to hold three trillion gallons of refreshingly clear water! Start your Sebago Lake day trip at Sebago Lake State Park. The park consists of over 1,400 acres of sandy beaches, woodlands, ponds, and waterways home to a diverse range of plants and wildlife. Spend the day on the hiking trails, biking the park roads, or on the water in a kayak available from the local marinas. If you are interested in fishing, check with the Maine Department of Inland Fisheries and Wildlife for information on fishing regulations. Combine your day trip with a unique boat tour on nearby Long Lake. Board the replica Mississippi paddle wheeler, the Songo River Queen II, for a one- or two-hour scenic cruise with spectacular views of the lake and surrounding area. 

**Due to the COVID-19 pandemic, hours at attractions may be limited. Make sure to check the websites and add to your list for future travels!