Things to Do in Maine
Maine is a state of rugged coastlines, charming seaside towns, and endless natural beauty, making it one of the most captivating places to explore in New England. From its iconic lighthouses and lobster shacks to its forests, lakes, and mountains, Maine offers a perfect balance of adventure and relaxation.
I’ve wandered along rocky shores, explored vibrant towns filled with local character, and enjoyed peaceful escapes surrounded by nature. Whether you’re planning a summer getaway on the coast, a fall foliage trip, or a winter retreat, Maine has no shortage of incredible things to do and experiences to enjoy. Here are the ones I recommend, and I think you’ll love them too.
1. Relaxing with ocean views in Freeport - just a 25-minute drive from Portland
From Portland, it was a quick 25-minute drive north to Freeport, a town of about 8,500.
Famous as the home of L.L.Bean since 1917, its flagship store is open 24/7 and anchors a walkable downtown packed with outlets and boutiques.
I stopped at the Freeport Historical Society ($5 donation) to learn about the town’s shipbuilding and farming past before exploring Harraseeket Harbor.
We stayed at Harraseeket Inn ($185), a classic New England lodge with cozy fireplaces and a locally sourced restaurant.
Freeport, Maine, turned out to be one of the coolest towns I’ve explored in New England, and honestly, it’s an absolute dream for a weekend getaway.
Just about 20 minutes north of Portland, I discovered that Freeport isn’t only famous for L.L. Bean—it’s packed with hidden gems that made my trip feel both exciting and special.
One of my favorite experiences was wandering through the outlets. I know shopping isn’t everyone’s thing, but here it felt unusually fun with so many affordable finds and a vibrant, bustling atmosphere that gave the town a joyful energy.
I also loved stumbling upon the Desert of Maine, which was one of the most unusual and underrated attractions I’ve ever seen in New England. It’s a quirky hidden gem where I walked across rolling sand dunes surrounded by forest—it felt so unique!
Wolfe’s Neck Woods State Park completely won me over. Hiking the wooded trails along the water and spotting ospreys was the kind of spectacular outdoor experience that makes Maine so magical. It felt romantic but would also be an awesome family adventure.
When I needed a food break, I found some of the best lobster rolls and clam chowder in cozy, casual spots that gave me a taste of real coastal Maine flavor. Those meals alone felt like an experience worth the trip.
For me, Freeport is a brilliant idea for a getaway—whether you’re into shopping, nature, food, or just unusual, interesting adventures, it has a little bit of everything, and that’s what makes it unforgettable.
2. Seaside Grace in Kennebunkport
From Portland, it was about a 40-minute drive south to Kennebunkport, a town of around 3,600 that has drawn summer visitors for over a century. The Dock Square area, with its 18th- and 19th-century buildings, was once a shipbuilding hub.
I browsed art galleries, souvenir shops, and lobster shacks before heading to the Seashore Trolley Museum ($12 admission), the oldest and largest electric railway museum in the world. We stayed at the Captain Lord Mansion ($235), a historic 1812 sea captain’s home turned elegant inn.
Kennebunkport, Maine, felt like stepping straight into a coastal dream, and it quickly became one of my favorite places for a romantic weekend or a joyful family escape.
About 30 minutes south of Portland, this charming town has the perfect mix of vibrant seaside energy and hidden gems that make every corner feel like an exciting discovery.
One of the absolute best things I did was stroll along Dock Square, where the colorful shops, art galleries, and cozy cafés gave me that small-town magic I love. It was so easy to get lost in the atmosphere.
I also hopped on a lobster boat tour, which turned out to be one of the most unique experiences of my trip. Learning how lobstermen work while cruising the harbor made me appreciate Maine’s heritage even more, and the views were spectacular.
For outdoor lovers, Goose Rocks Beach was a highlight. Its soft sand, wide shoreline, and peaceful waves created a joyful, relaxing vibe—perfect for a morning walk or a romantic sunset stroll.
My favorite foodie moment was digging into a buttery lobster roll at one of the waterfront shacks. Honestly, it was the best I’ve had, and it felt like an iconic Maine experience I’ll never forget.
Kennebunkport also has some of the coolest historic inns and boutique hotels, each with their own unique flair. Staying overnight made the whole trip feel like a complete New England getaway filled with magic and charm.
3. Bloom and awe at Coastal Maine Botanical Gardens
From Portland, it was about a 1-hour 15-minute drive northeast to Boothbay.
Stepping into the Coastal Maine Botanical Gardens in Boothbay Harbor felt like discovering a hidden gem nestled on Maine’s spectacular coast.
Just over an hour north of Portland, I found that this verdant paradise is the absolute best place to connect with nature, art, and thoughtful design all at once.
We wandered through the Lerner Garden of the Five Senses, a unique, imaginative haven that delighted every sense—from fragrant herbs to cascading water—my favorite sensory experience of the trip.
I also adored the Bibby and Harold Alfond Children’s Garden, where whimsical play areas, storybook themes, and a maze made it an awesome family-friendly escape.
Hunting for the Guardians of the Seeds—those giant, magic troll sculptures by Thomas Dambo—was an exciting, unusual adventure through the forests and shoreline.
The Bosarge Family Education Center—a brilliant idea turned reality as Maine’s greenest building—captivated me with its eco-friendly architecture and net-zero energy design.
We also strolled grassy paths around Whale Rock on the Great Lawn, and relaxed by the serene Vayo Meditation Garden, giving the gardens a romantic, restful spirit.
Themed gardens throughout—like the Dahlia Garden, Burpee Kitchen Garden, Fairy House Village, and Learning Apiary—made every section of the Gardens feel extraordinarily unique and delightful.
We savored a snack in the café, browsed locally made treasures in the Gardenshop, and enjoyed a cheerful picnic among the blooms—a truly affordable yet magical experience.
Whether you're a gardening enthusiast, art lover, or simply seeking tranquil beauty, the Coastal Maine Botanical Gardens is the most spectacular, under-the-radar escape in Maine—and an absolute must-see on any Mid-Coast itinerary.
4. Harbor Light & Hops in Portland, Maine
We flew from Austin to Portland (about 4 hours with a layover, fares around $200–$320 round trip) and landed in a compact city of roughly 68,000. Instead of renting a car, we explored Portland on foot and by bus. The METRO Route 8 looped us to the waterfront and the arts district ($2 fare).
We browsed the Portland Museum of Art ($18 admission), walked Deering Oaks Park (55 acres with ponds and trails), and capped the day with oysters and craft beer in the Old Port. For lodging, we booked the Portland Harbor Hotel ($185), centrally located and easy for a car-free visit.
Portland, Maine, completely won me over with its vibrant mix of coastal charm, foodie magic, and hidden gems that made every moment feel like a dream getaway.
Set right on Casco Bay, this lively city is just two hours from Boston, but it feels like an entirely different world—laid-back, scenic, and filled with unusual experiences I didn’t expect.
My favorite part was exploring the Old Port, with its cobblestone streets, cool boutiques, and some of the best seafood shacks I’ve ever tried. Walking here felt both romantic and exciting, with that perfect mix of history and modern energy.
I couldn’t resist hopping on a ferry out to Peaks Island, and the short ride gave me spectacular bay views. Once there, I biked around the shoreline, which was such an underrated and joyful adventure.
For foodies, Portland is an absolute gem. I tasted buttery lobster rolls, fresh oysters, and even stopped at award-winning bakeries that made me rethink how good a croissant could be. Honestly, this city is one of the best foodie destinations in New England.
Art and culture lovers will be thrilled too—I explored the Portland Museum of Art and found unique galleries tucked into side streets that added an interesting, creative vibe to the city.
What I loved most was how Portland mixes big-city cool with small-town warmth. Whether it’s strolling the Eastern Promenade, taking a brewery tour, or just soaking in ocean views, it’s the kind of place that feels both lively and relaxing all at once.
For me, Portland is one of the most spectacular and memorable coastal cities in Maine—an affordable, exciting, and unique destination worth every minute.
5. Sailing stories on the Schooner Stephen Taber
From Portland, it was about a 1 hour 45-minute drive northeast to Rockland, a city of roughly 7,000. Once a shipbuilding and lime-processing hub, today it’s known as the Lobster Capital of the World.
Sailing aboard the Schooner Stephen Taber in Rockland, Maine, was one of the most magical and unusual adventures I’ve ever had on the coast.
This National Historic Landmark, launched back in 1871, is actually the oldest documented sailing vessel in continuous service in the United States, and experiencing it firsthand felt like stepping back in time while still enjoying the best of modern comfort.
I loved the feeling of raising the sails alongside the crew—there was something joyful and unforgettable about being part of the action instead of just watching.
Drifting past hidden coves, lighthouses, and the spectacular rocky shoreline of Penobscot Bay, I found myself constantly reaching for my camera. Every angle was postcard-perfect, and the sunsets were absolutely breathtaking.
Meals onboard turned out to be one of my favorite surprises. Fresh, locally sourced dishes prepared in the ship’s galley felt like an exceptional Maine culinary experience at sea, often enjoyed on deck with ocean breezes and views that made it even more memorable.
Sleeping in a cozy wooden cabin gave me that rare mix of rustic charm and romantic nostalgia. Waking up to the sound of gulls and the gentle rocking of the schooner was honestly a dream come true.
What makes the Schooner Stephen Taber such a hidden gem is how it combines history, adventure, and relaxation. It’s not just a sail—it’s a spectacular coastal Maine experience, one of the coolest getaways I’ve ever had, and something I’d recommend to anyone looking for a unique, unforgettable trip.
6. Riding the rails of nostalgia at Seashore Trolley Museum
From Portland, it was about a 40-minute drive south to the Seashore Trolley Museum, founded in 1939. The museum preserves more than 250 transit vehicles, from horse-drawn streetcars to vintage electric trolleys from across the U.S. and abroad.
Admission was $13 for adults, which included unlimited trolley rides along a 1.5-mile restored section of the old Atlantic Shore Line Railway.
Walking through the barns, I saw everything from early Boston streetcars to rare European trams. We stayed at the Kennebunkport Inn ($195), just a short drive away in Dock Square.
Visiting the Seashore Trolley Museum in Kennebunkport turned out to be one of the most unique and underrated experiences I’ve had in Maine.
Just a short drive from the coast, this hidden gem completely transported me back in time with its fascinating collection of historic streetcars, trolleys, and transit vehicles from around the world.
I loved stepping onto the beautifully restored trolleys and actually riding along the museum’s heritage railway—it was such a joyful and unusual way to experience history in motion.
My favorite moment was sitting in one of the open-air electric trolleys, feeling the breeze and listening to the conductor’s stories. It made the whole experience feel both magical and personal.
For families, the museum is an absolute dream. Kids can climb aboard different vehicles, explore exhibits, and even watch restoration work in progress, which makes it both fun and educational.
I was amazed at how vibrant and international the collection was—there were pieces from Boston, New York, Philadelphia, and even as far away as Europe and Asia. It’s the coolest mix of local and global history all in one place.
The volunteers were exceptional too, sharing their passion and knowledge with such excitement that it added a whole new layer to the visit.
What I found most brilliant is how affordable and family-friendly it is, yet it feels like an extraordinary adventure. For me, the Seashore Trolley Museum isn’t just a museum—it’s a living, moving, and spectacular piece of history that makes Kennebunkport even more special.
7. Art and quiet brilliance at Colby College Museum
From Portland, it was about a 1 hour 15-minute drive north to Waterville.
Exploring the Colby College Museum of Art in Waterville, Maine, felt like stumbling upon one of the most underrated cultural gems in New England.
Set on Colby’s beautiful campus, just about an hour north of Portland, the museum completely surprised me with its vibrant collection and welcoming atmosphere—it’s free, which makes the experience even more amazing and accessible.
I loved wandering through the galleries and discovering an exceptional mix of American art, from classic works to bold contemporary pieces. The collection includes some of the best Wyeth family paintings, which felt like a true Maine treasure to see in person.
One of my favorite moments was stepping into the modern galleries filled with large-scale installations and unique sculptures that gave the museum a cool, cosmopolitan vibe, even in this quiet college town.
The museum’s Lunder Collection absolutely blew me away. With works by Whistler, Remington, and O’Keeffe, it felt like an unusual and spectacular surprise to find such masterpieces tucked into central Maine.
I also enjoyed the way natural light filled many of the galleries, making the art feel alive and dynamic. It created a joyful and inspiring atmosphere that encouraged me to linger longer than I expected.
Whether you’re looking for a family-friendly outing, a romantic cultural stop, or just a hidden gem to explore on a weekend getaway, the Colby College Museum of Art is one of the coolest, most affordable, and most magical experiences in Maine.
8. Wiggly Bridge Distillery
From Portland, it was about a 45-minute drive south to York, a seaside town of around 13,000. Wiggly Bridge Distillery takes its name from a tiny suspension bridge built in the 1930s that still “wiggles” as you walk across it. p>I was completely taken by the story—this distillery started as a family project and has grown into one of the most amazing and underrated places to visit in Maine. To me, that made the experience even more joyful and inspiring.
What I loved most was how hands-on everything felt. I got to see the actual copper stills (built by hand!) and taste some of the smoothest spirits I’ve ever tried. Their bourbon quickly became one of my favorites, but I also thought the rum was exceptional.
Being in such a cozy space made the whole tasting feel intimate and special. It didn’t feel touristy at all—more like discovering a cool, unusual gem that only locals whisper about. I thought that was the magic of it.
For me, the cocktails were an absolute highlight. I tried one with their gin that was not only affordable but also one of the best drinks I had all weekend. You can see in my photos how vibrant and inviting the space felt.
If you’re planning a weekend getaway in southern Maine, I honestly think Wiggly Bridge Distillery is a brilliant idea—whether you’re on a romantic trip or just a fun family adventure, it’s one of the best stops to make.
Conclusion:
At the end of the day, what makes Maine so special is the variety of experiences it offers. From hidden distilleries like Wiggly Bridge to spectacular coastal towns, lighthouses, and vibrant food scenes, every corner of the state feels like a new discovery. I always find something unique here, whether it’s exploring the rugged coastline, enjoying a family-friendly adventure, or soaking in a romantic weekend getaway. The coolest part is that Maine never feels overdone—it’s still filled with underrated gems and unusual experiences that make every trip exciting. For me, Maine isn’t just a destination; it’s a place where every visit feels magical, memorable, and absolutely worth returning to again and again.
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