By Jamie Edwards, award-winning travel writer who’s visited 70+ countries on all 7 continents
Portland, Maine makes a persuasive case for staying put. Between the harbor’s salty air, working waterfront, and lively food scene, you could plan an entire trip without ever crossing the Casco Bay Bridge. Yet, some of Portland’s most fabulous finds lie about an hour or so beyond it.
Trade the city’s buzz for windswept beaches and schooner-lined harbors. Depending on the season, there are plenty of easy escapes that can deepen your Maine experience—from brighter fall foliage and quieter spring coastlines to festive winter traditions and classic summer beach days. Call Portland home? Chances are, there are a few of these day trips you’ve always meant to do—but haven’t gotten around to just yet.
Why wait? Follow along for six fun day trips designed for those who seek variety, for families who’d love to plan weekends beyond their kids’ soccer tournaments, and for couples who want a dramatic water view paired with a savory lobster roll.
In Maine, Timing is Everything
When planning a trip from Portland, a little foresight goes a long way. Maine’s rhythms shift with the seasons, shaping everything from traffic to restaurant availability, ferry schedules, and even the quality of the light along the coast—a very important note for photographers and artists.
Summer delivers peak beauty but also peak crowds, while spring, fall, and winter each offer distinct, quieter versions of Maine that reward early planning in different ways. Thinking about how you structure your days can mean the difference between seamless travels and hours spent inching along Route 1. A few tips follow:
- Plan for early summer to avoid parking bottlenecks and traffic congestion.
- Shoulder season (May/June and Sept/Oct) brings less congested roads and easier restaurant bookings.
- Pack layers even in summer; coastal evenings cool fast.
- Consider plotting day trips from the closest first. As always, CIRE can help plan the details.
Let’s plot our Portland, Maine trips in that very order. Starting with the closest first, here are six Portland day trips to fill up your year. Fill up the tank, we’re heading out of the city.
Biddeford, Maine
Drive time: About 25 minutes from Portland (roughly 18 miles). Biddeford is the lowest-effort day trip on the list.
Why go? This former mill town has become a dynamic, low-key food destination. Chefs, bakers, and baristas are building something exciting in Biddeford. It’s close to Portland but different enough to feel like you really got out of town. Between brick mills, the downtown river views, and a compact main drag filled with bites and snacks, Biddeford is Maine’s most satisfying “come for lunch, stay for the vibe” detour.
When to go? Fall and winter are Biddeford’s sweet spots. When coastal towns slow down, Biddeford stays lively—and a meal-driven day trip feels especially rewarding. Bonus: It’s typically easier to snag a weekday table than during peak summer weekends.
Spotlight: Plan your day around the food scene in Biddeford; it’s the main draw.
Lunch break: If you can time it right, lunch at Palace Diner is the way to go. Is there a line? Treat it like a part of the experience: stroll downtown, grab a coffee, and come back when your name is called. Palace is a tiny, beloved diner with an outsized reputation.
Worth knowing: Biddeford is a walkable, low-planning day trip, but parking and peak lunch and brunch lines can be a factor, especially on weekends. One strategy is to arrive earlier than you think you need to and build your day around a flexible food crawl rather than a single fixed reservation.
Best way to spend the day: Start with an early lunch/brunch, add a coffee and quick browse through the downtown area, take a short stroll along the river to reset between stops, then pick up something sweet for the short ride back. (There are also some legendary dive bars in Biddeford, too, if that’s your scene.)
The Kennebunks (Kennebunk and Kennebunkport)
Drive time: The drive from Portland to Kennebunkport is about 36 minutes (roughly 28 miles), making it an easy half or full-day outing.
Why go? The Kennebunks deliver that full coastal New England day-trip feeling. It has beautiful stroll-worthy streets, boutiques and galleries to browse, and shoreline scenery that’s picture-postcard perfect. It’s an easy, high-reward escape from Portland.
For those curious about the difference between these two adjacent Maine towns, Kennebunk is the quieter, more residential inland half, with classic village charm, and Kennebunkport is the harbor-centric, stroll-and-shop seaside sibling.
When to go? Summer for peak harbor energy, picnic table lobster rolls, and boating season. September is the sweet spot, when it’s warm enough for a beach walk, the town is noticeably calmer, and it’s often easier to park. Early December is a festive bonus if you want holiday atmosphere: the area’s Kennebunkport Christmas Prelude brings lights, events, and a wintery coastal charm.
Spotlight: Park once and wander. Start at Dock Square, the heart of Kennebunkport, where the harbor vibe, shops, galleries, and people-watching all come together in a few lively walkable blocks.
Lunch break: Maine is known for lobster rolls and clam shacks. What better place to experience this local culinary highlight than in Kennebunkport? Lean into coastal classics on the riverfront at Arundel Wharf or make some new friends as you line up at the famous Clam Shack. If you’re going in the summer, remember to plan lunch slightly early or late to avoid the peak rush. Should you decide to experience Kennebunkport in the off-season, Little Barn is a great bet.
Worth knowing: The Kennebunks are uber-popular for a reason. The easiest strategy (do you detect a theme?) is to arrive early, keep your schedule loose, and avoid a rigid plan. Let the town take you down narrow alleys and into nautical boutiques.
Best way to spend the day: Start in Dock Square for some essential window shopping. Have an early lunch near the harbor, then take a drive out to Goose Rocks Beach for a long walk and an ocean air reset. If time allows, catch golden hour back near the water before returning to Portland.
Ogunquit, Maine
Drive time: Roughly 37 miles and about 44 minutes from Portland. Close enough to be spontaneous!
Why go? If Kennebunkport is about polished harbor charm, Ogunquit is about pure coastal scenery and simple beauty. It’s one of those places where cliff-side walks feel movie-like, with crashing surf, salty air, and views that make you stop in your tracks. The best part? A day trip here doesn’t require any complicated planning.
When to go? In early fall or late spring, Ogunquit is still luminous, the crowds are fewer, and the crisp, refreshing air lingers on. Summer is classic if you want beach time and buzzy energy, but expect peak crowds, too.
Spotlight: Don’t miss Marginal Way, a 1.5-mile ocean-hugging cliff walk that leads you right into Perkins Cove—a tiny, storybook harbor of wooden docks, colorful lobster boats, waterside galleries, and eateries clustered at the water’s edge. It’s one of the most beautiful stretches of coastline in southern Maine.
Lunch break: Beeline to M.C. Perkins Cove for a classic lobster roll or a seafood lunch with great water views. If it’s busy, grab something to-go and find a perch by the harbor to admire the views.
Worth knowing: If busy, walk Marginal Way in the morning light, and save town or beach time for later in the day.
Best way to spend the day: After your morning walk and lobster roll, spend the afternoon at the beach or duck into a few art galleries before heading back to the city.
Portsmouth, New Hampshire
Drive time: About 54 minutes from Portland (roughly 52 miles). Portsmouth is one of the best cross-state day trips from Maine.
Why go? Portsmouth brings a more urban energy to the day-trip mix. It’s historic, walkable, and lively, with a seaport setting that feels like a mini city break.
When to go? Late spring through fall is best, especially summer and early fall, when long daylight hours make it easy to pass the hours on the waterfront and patios. It’s when the city feels most vibrant and alive.
Spotlight: Portsmouth’s working waterfront is where tug boats and sailboats glide past historic brick buildings. This blend of maritime grit and preserved colonial architecture is part of what gives Portsmouth its distinct character.
Lunch break: Portsmouth is made for a leisurely lunch. Choose a spot downtown or by the water, like Surf Seafood, so you can continue aimlessly wandering afterward. In summer and early fall, outdoor tables are reserved for early birds.
Worth knowing: This is a park-once destination, but weekends can still get busy, especially in peak summer. If you’re going on the weekend, arriving earlier will make your day go much smoother.
Best way to spend the day: Begin around Market Square, and follow the brick sidewalks that lead you through shops, galleries, and down toward the waterfront. After a relaxed lunch downtown, spend your afternoon at the Strawbery Banke Museum for a dose of living history. If you’re visiting in summer, stroll through Prescott Park for garden blooms and harbor views.
Boothbay Harbor, Maine
Drive time: Just over an hour from Portland (roughly 57–58 miles), Boothbay Harbor is a comfortable full-day excursion.
Why go? If southern Maine feels close and intimate, Boothbay Harbor introduces the quieter, more expansive feel of the Midcoast. It’s a classic coastal village with a built-in main event: the Coastal Maine Botanical Gardens. The town itself is unfussy: boats bob in the harbor and seafood shacks and small shops abound. But the gardens elevate the day—a must-see!
When to go: Summer for harbor energy and long sun-kissed evenings. Late November through December for Gardens Aglow, when the botanical gardens transform into a holiday light extravaganza. It’s arguably one of Maine’s most festive winter outings.
Spotlight: Time your visit to the botanical gardens for mid-to-late afternoon light in the early summer, when the sculptures, waterfront trails, and seasonal plantings are especially photogenic.
Lunch break: Lean into harbor views, fresh seafood, lobster rolls, or a simple waterside lunch before or after your garden visit. In summer, aim for an earlier seating to avoid peak waits. The botanical gardens have an on-site restaurant with a rotating seasonal menu that’s worth noting.
Worth knowing: Plan your timing around the Coastal Maine Botanical Gardens. The grounds are expansive and best enjoyed at a relaxed pace.
Best way to spend the day: Ease into the day by circling Boothbay Harbor’s waterfront and sipping espressos with a view of the water. If you’re visiting in the colder months, spend daylight hours in town, then return after dark for Gardens Aglow, when the grounds take on a festive glow.
Camden, Maine
Drive time: Our furthest day-trip destination is only 1 hour 37 minutes from Portland (about 81 miles), making it best suited for a true full-day outing.
Why go? Camden is the quintessential postcard harbor day: sailboats in the foreground, green hills rising behind town, and a crisp coastal light that makes everything look luminous. It’s compact but layered. Browse, hike, sail, and enjoy a long leisurely lunch all within a small, walkable radius.
When to go: Fall (late September through mid-October) is exceptional, when foliage lights up the hills. Summer brings peak sailing season, longer daylight hours, and classic harbor energy.
Spotlight: The view from Camden Hills State Park, especially at the Mount Battie overlook. Whether you hike up or drive to the summit, the sweeping harbor-and-islands panorama is Camden’s signature moment.
Lunch Break: Choose a harbor-facing spot along Main Street, like The Salt Wharf, so you can feast on fresh seafood while watching the boats drift in and out. In summer, an outdoor table is worth the wait.
Worth knowing: It’s tempting to rush from harbor to summit and back again, but the magic is in layering the experiences—sit and absorb the view rather than treating it as a quick Instagram photo op.
Best way to spend the day: Arrive mid-morning and wander the harbor and Main Street. Visit the galleries and boutiques at your own pace. Late morning or early afternoon, head to Camden Hills State Park for the view from Mount Battie. Should you have time, upgrade your day trip with a harbor sail aboard a traditional schooner.
Day Trippin’
Portland may be one reason many travelers come to Maine, but the beauty of staying there is how easily you can experience so much more. Within a short drive, the landscape shifts from lively harbor towns to beautiful coastlines, historic streets, and quiet coastal vistas, each offering a distinct perspective on the state’s character and natural charm. In every season, these escapes reveal a different side of Maine.
Whether you arrive as a visitor or have long called this place home, these day trips prove that sometimes the best way to get to know a city is to step just beyond it.
Note: Many restaurants operate on seasonal schedules, so it’s worth confirming opening hours ahead of your visit.
Jamie Edwards is an avid traveler, travel writer, and photographer. After 25 years of living and traveling around the globe, she launched I am Lost and Found, her adventure/luxury travel website. Jamie’s goal is simple: to inspire travel.
CIRE Travel is a full-service travel agency headquartered in New York, NY with offices in Kennebunkport, ME, Washington DC, Boston, MA, Atlanta, GA, Los Angeles, CA, and Philadelphia, PA. Our expert corporate travel planners, honeymoon travel agents, and luxury travel planners support clients across the country and around the world.
Where in the World Do You Want to Go?
Inspired to plan your next weekend getaway, vacation or trip of a lifetime? See that form below? That’s all it takes to begin your next epic travel story.