Maine road trip: 10 must-see towns and fun things to do

Greenvans transit van parked in driveway by a tree at sunset

Attention! If you’re someone who likes to hike and kayak, discover art and history, chow down on fresh seafood, and uncover the country’s most incredible landscapes, you need to plan a trip to Maine, immediately.

Maine has it all — stunning wildlife, towering mountains, seaside villages, lively festivals, local breweries, water sports…the list goes on. Active families and groups of friends are the perfect candidates for a trip to what is arguably New England’s prettiest state. 

Read through our list of 10 must-see towns and things to do in “the Pine Tree state”, all of which are easily reached in one of our Boston van rentals! After you secure a comfortable van, it’s time to pack your bags and hit the road on a Maine road trip, one of the most beautiful journeys in the United States!

1. Acadia National Park

In our expert list of 20 best places to camp across the country, Acadia National Park clocks in at number two. Even if you’ve got no plans to pitch a tent, a Maine road trip without a stop at the oldest national park in the Eastern U.S. wouldn’t be a Maine road trip at all! Not only is it home to the country’s only fjord, its famous Cadillac Mountain is the highest peak on the Atlantic coast with views that cannot be captured anywhere else in the world.

Pass a full day hiking the spectacular trails or swimming in the crystal-clear waters of Jordan Pond. Rent a van from Providence to comfortably enjoy the scenic drive along Park Loop Road. Pack a picnic lunch or take a five-minute drive to Bar Harbor to dine in a local seafood restaurant.

2. Portland

Artsy, historic, and overflowing with fresh seafood, Portland is one of Maine’s most vibrant and interesting towns. Start with a visit to the iconic Portland Head Light for a stroll along the rugged cliffside and the expansive Atlantic Ocean. 

In the afternoon, wander the Old Port district, whose cobblestone streets bubble over with art galleries, boutique shops, and charming cafes. Feeling hungry? It’s time to make your way to the waterfront district to feast on lobster rolls and freshly shucked oysters. Beer lovers will delight in the abundance of local breweries in town, like Allagash and Shipyard, which are also open for tours and tastings.

If you plan to spend a night or two, sign up for a scenic cruise of Casco Bay and enjoy an afternoon on the water with beautiful views of the shoreline peppered with lighthouses.

Photo by Keith Luke on Unsplash


3. Camden

Mountains meet the sea at this picturesque seaside village on Maine’s scenic coast. Start your getaway with a visit to Mount Battie and Camden Hills State Park, where you can spend the morning hiking, picnicking, and enjoying the natural landscape. 

When you’re ready to return to civilization, drive just five to ten minutes to the center of town, stopping in the Owl & Turtle Bookshop Cafe to browse its quirky collection of books. If weather permits, embark on a sailboat excursion around Penobscot Bay. 

In the evening, dine on fresh fish and perhaps catch a show at the Camden Opera House. A Maine road trip any time of year is nice, but it’s especially peaceful between April and June. These months guarantee smaller crowds and temperate weather, making for a more relaxed vacation experience. 

Photo by Brad Weaver on Unsplash

4. Kennebunkport

If you’re planning a Maine road trip during the heat of the summer, definitely  include a stop in Kennebunkport. Why? Because it’s basically the water sports capital of Maine, that’s why! There are so many things to do on the bay; from leisurely activities like sailing, lobster boating, and whale watching, to more strenuous outings, like kayaking and canoeing.

Home to famous community art teacher Bob Paine, art enthusiasts can browse the W. Robert Paine Gallery before perusing the local galleries at Dock Square. History buffs can check out the Seashore Trolley Museum, a short drive away. 

For those who prefer an off-season Maine coast road trip, Parsons Way is excellent for hiking due to its coastline views and is especially pretty during spring or fall. No matter the season you choose, though, the abundance of nature and vibrant activity in town make Kennebunkport an ideal year-round destination for families and friends.

Photo by Chris Jones on Unsplash

5. Cape Elizabeth

Explore, relax, eat, repeat. This is a day in the life of a vacationer at Cape Elizabeth. If you have no plans to visit Portland on your Maine itinerary, take this opportunity to drive 12 minutes to see the famous Portland Head Light. 

Head back south to spend a leisurely day on the sandy beaches of Crescent Beach State Park. Need a break from all that relaxing? There are lots of scenic walking trails here to incorporate into your day.

Late afternoon, explore the town’s historical sites including the Spurwink Meeting House, a historic church and spooky cemetery from the early 1800s. Round out your laid-back seaside experience with a locally famous lobster roll at The Lobster Shack at Two Lights.  

6. Skowhegan

Located in the heart of Maine on the Kennebec River, Skowhegan is both scenic and brimming with outdoor recreation. The eclectic mix of historical sites, river activities, and cultural experiences is more than enough to fill a one-day getaway.  

Water sports lovers can venture to the river for fishing, kayaking, and canoeing, while history aficionados learn about the town’s past at the Skowhegan History House Museum & Research Center and its old-fashioned gardens. The art scene pulses with life, with galleries galore and interesting exhibits at the School of Painting & Sculpture. When you’re ready to chill, downtown Skowhegan is home to boutique shops and local eateries.

Should you plan a trip to Maine in August, don’t miss one of the longest-running fairs in the U.S.! The beloved Skowhegan State Fair has been a family-friendly event in production since 1818, complete with carnival rides, live entertainment, agricultural exhibits, and food stalls. 

7. Rockland

Maine is indeed an artsy place, but no town does it quite like Rockland. From the extensive American art collection at Farnsworth Art Museum to the talented Wyeth family’s works at Wyeth Center, art lovers will keep quite busy.

For a bit of sightseeing, take a tranquil stroll along the wild shoreline to Rockland Breakwater Lighthouse, a historic and iconic New England landmark that cannot be missed. If you plan a trip to Maine between May and July, sign up for a sailing tour to see puffins nesting on the coast.

In August, Rockland hosts the Maine Lobster Festival, five delectable days of entertainment, cooking contests, games, and, of course, fresh lobster served in a variety of ways! It’s an unforgettable and very New England-esque experience that you’ll be happy to witness.

Photo by Karl Magnuson on Unsplash

8. Bar Harbor

Speaking of, this vibrant town is a must-see on your Maine itinerary. Opt to combine a visit with an active morning at Acadia National Park, or take a full day of leisure exploring quaint Bar Harbor. 

Stroll along Shore Path, a short coastal stretch that passes by the historical Bar Harbor Inn, Balance Rock, and Nelson Rockefeller’s birthplace. Make your way downtown to explore artisanal delicatessens and boutique stores before settling in at a delightful restaurant offering local seafood dishes.

Late May to September sees a lot of marine activity, making the summer and early fall an ideal time of year to sign up for a whale-watching tour. This is a memorable and highly unique experience that the whole family is sure to enjoy!

Photo by Falling Further on Unsplash

9. Monhegan Island

If you want to “get off the grid”, plan a trip to Maine’s Monhegan Island. Great for a day’s visit or an overnight, the tiny island is made up of hiking trails, artist studios, rocky beaches, and one museum. 

The island is only accessible by ferry, providing lots of opportunities for marine life sightings on the journey. Upon arrival, explore its nine miles of nature paths that lead to rocky cliffs and ocean views before making your way to the village. Here, visit the Monhegan Museum of Art & History for a dive into the island’s unique culture. 

Because a day on Monhegan Island is meant to be a relaxed one, allow yourself a good chunk of time to live like the locals do. Sip on a craft ale in Monhegan Brewing Company’s tasting room before a seafood feast at The Barnacle or Island Inn.

10. Bangor

Made famous by award-winning author Stephen King, Bangor has so much more to offer besides a possible glimpse at the man who brought It to life. Peruse 20th-century masterpieces by the likes of Andy Warhol, Andrew Wyeth, and Pablo Picasso at the University of Maine Museum of Art. Pop over to Maine Discovery Museum and see its interactive exhibits designed specifically for the little ones.

The Penobscot River provides opportunities to kayak, fish, and hike the riverbank. It’s also the site of Bangor’s Waterfront Park, where visitors can walk past sculptures and food trucks on the riverside trail. Reserve a table for dinner at The Tarrantine, known for using seasonal products as the base of its creative dishes.

The ultimate Main road trip itinerary

Maine is a truly beautiful state with a one-of-a-kind culture. It’s also small, meaning the best way to move from one destination or another is by van. If you’re planning a Maine road trip, the most logical way to schedule your stops is from south to north along the coast, cutting westward upon leaving Bar Harbor. 

Starting from the southern border, we suggested stopping at the following locations in this order:

  • Kennebunkport
  • Cape Elizabeth
  • Portland
  • New Harbor to board the ferry to Monhegan Island 
  • Rockland
  • Camden
  • Bar Harbor which serves as a great base to visit Acadia National Park
  • Bangor
  • Skowhegan

From Skowhegan, you can drive back south along the coast or opt for a detour to one of our favorite New England winter getaways, the White Mountains in North Conway, New Hampshire.

How to road-trip to Maine

Maine is the cherry on top of any East Coast road trip. If you’re starting in Boston, New York, or even Florida, make your way north to New England’s crown jewel keeping the below itineraries in mind.

Boston to Maine road trip ideas

There are wonderful seaside destinations on a road trip from Boston to Maine. If you’re looking to make as many stops as possible, check out Boston to Portland, Maine: 15 destinations that make the ultimate road trip. Once you’ve hit Portland, continue exploring with the itinerary above.

Starting from Boston, don’t miss visits to:

  • Salem, Massachusetts
  • Rockport, Massachusetts
  • Gloucester, Massachusetts
  • Newburyport, Massachusetts
  • Portsmouth, New Hampshire

From Portsmouth, head toward Kennebunkport and continue with our ultimate Maine road trip itinerary. 

Philadelphia to Maine road trip itinerary

A journey from New York to Maine is especially ideal for anyone flying into JFK International Airport from another part of the country. Rent a van in Philadelphia and plug the following locations into the GPS. When you’ve arrived in Maine, continue with the above itinerary. 

From New York City, make your way north to:

  • Stamford, Connecticut
  • New Haven, Connecticut
  • Newport, Rhode Island
  • Providence, Rhode Island 
  • Boston, Massachusetts
  • Salem, Massachusetts
  • Portsmouth, New Hampshire

From Portsmouth, head toward Kennebunkport and continue with our ultimate Maine road trip itinerary. 

Suggestions for a Florida to Maine road trip

A Florida to Maine road trip is one of the most emblematic journeys in the country. Route 1 is teeming with history, natural beauty, and thriving urban hubs. It’s one of our favorite cross-country road trip routes due to its proximity to the ocean and exciting mix of cultures. 

Suggested stops along the way include:

  • Key West, Florida
  • Miami, Florida
  • Savannah, Georgia
  • Charleston, South Carolina
  • Washington, D.C.
  • Philadelphia, Pennsylvania
  • New York, New York

From here, follow the New York to Maine itinerary above. If you happen to be driving during leaf-peeping season, take a detour through the Berkshires to soak up the colorful landscapes of Massachusetts in autumn.

Explore Maine in style

A Maine road trip is something everyone should do at least once in their lifetime. There are so many amazing things to do here — wildlife lovers can watch whales in Bar Harbor, active travelers can hike in Acadia National Park, and art enthusiasts can contemplate famous works in Rockland. 

Enjoy fresh lobster and a craft beer after a day in a kayak or hike to an iconic lighthouse for a family picture. Moving between destinations is a cinch. Attractions and destinations are so close together, all it takes is booking a stylish van rental with Greenvans, setting up your GPS with the itineraries above, and hitting the road for a New England adventure you’ll never forget.

The ultimate Maine road trip awaits.


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