The Perfect Day Trip to Portland, Maine | Lighthouses, Tours & the Best Local Eats

Planning the perfect day trip to Portland, Maine? As the innkeeper here at Wolf Cove Inn, I love helping guests make the most of their time in our beautiful state. Breathtaking lighthouses, coastal parks, and downtown foodie spots—here’s a go-to itinerary we love sharing with our guests.

Just a note: Be sure to check ahead as some locations have seasonal availability.

“The rocky ledge runs far out into the sea, And on its outer point, some miles away,
The lighthouse lifts its massive masonry, A pillar of fire by night, of cloud by day.”
– Henry Wadsworth Longfellow, “The Lighthouse”

Kick off your day with a visit to Portland Head Light in Cape Elizabeth. It’s the most photographed lighthouse in Maine—and for good reason. Perched on a dramatic cliff where Casco Bay meets the Atlantic, it’s been guiding ships since 1791 (yes, it was commissioned by George Washington himself).

The tower itself isn’t open, but the Museum at Portland Head Light is tucked inside the former Keeper’s Quarters. It’s open seasonally (Memorial Day to Columbus Day) and packed with cool lighthouse lenses, maritime artifacts, and photos.

Right next door is Fort Williams Park, a 90-acre waterfront playground filled with:

• Easy walking trails and picnic spots. The main trail is paved and runs along the cliff’s edge (no worries—there’s a fence along the edge). It has benches at various points where you can stop to rest. Great way to stretch your legs and appreciate some of Maine’s natural beauty.

• Battery Keyes and Battery Blair: military remnants from the early 1900s.

• The ruins of Goddard Mansion, which makes for an excellent photo op.

• A Children’s Garden and cliffside meadow restored by the park’s Ecology Project/

From there, take a scenic drive south on Route 77 to Two Lights State Park. It’s got killer views of the headlands and a spot to relax and watch ships pass by.

While you're in the area, head to the Lobster Shack at Two Lights for lunch. It’s a Maine classic—fresh lobster rolls, chowder, fried clams—all served picnic-style right by the crashing surf. It’s hands-down one of the most authentic coastal dining experiences around.

Once you’ve had your fill of ocean air and seafood, it’s time to explore things to do in Portland itself. The city’s got that perfect blend of salty, historic charm and modern vibe. Our guests always rave about the walkable neighborhoods and fun, laid-back atmosphere.

Portland is super walkable, and Greater Portland Landmarks has fantastic self-guided walking tours:

• Old Port District — cobblestones, boutiques, and maritime history

• Congress Street Tour — a crash course in Portland’s architecture

• Western Promenade Tour — hilltop mansions and harbor views

• Munjoy Hill & Portland Observatory — the only maritime signal tower still standing in the U.S.

You could easily fill a few hours visiting these:

• Victoria Mansion — ornate Italianate-style home with original furnishings

• Wadsworth-Longfellow House — the poet’s childhood home

• Portland Museum of Art — an impressive mix of classic and contemporary works

• Colonial Tate House — the only colonial-era home open to the public in Portland
  
  

Want to add a little adventure to your day? Portland has plenty of ways to explore beyond walking:

• Five Lighthouse Tour — includes a stop at Portland Head Light

• Bike & Brews Tour — pedal and taste your way through local breweries

• Casco Bay Ferry + Island Tour — hop off and explore coastal island communities

• LuckyCatch Cruises — join a working lobster boat and haul traps

• Odyssey Whale Watch — spot whales, dolphins, and lighthouse views from the water

• Portland Schooner Co. — sail a historic windjammer around Casco Bay

• Portland Paddle — kayak or paddleboard right on the bay

• Maine Narrow Gauge Railroad – a waterfront ride with a mini museum to explore. For a seasonal treat, take a ride on their Polar Express.

Foodies, you’re going to love Portland. I always say you can’t go wrong with these spots—some are so popular our guests plan around them! These are just a few of the amazing options available. Again, be sure to call first for current hours.

• Fore Street — this place is wicked good with its wood-fired cooking and nod to local ingredients

• DiMillo’s On The Water — a floating fine dining restaurant with harbor views

• Portland Lobster Company — casual outdoor spot with live music (seasonal)

• Butcher Burger — unique burgers, lobster rolls, and more, all “made with love”

• Paper Tiger — fast food with a twist

• Scales — some consider this the best restaurant in the northeast

 

After all that exploring, come back to Wolf Cove Inn and kick back by the lake. We’re just about 45 minutes from Portland, but it feels like a world away.

These are some of the things you’ll experience here:

• An organic, local, farm-to-table delicious breakfast to start each day

• The culinary delights from our chef with our signature dinners

• Complimentary use of our kayaks and canoes on Tripp Lake

• A place to unwind by the fire pit (bring your favorite s’more ingredients for a sweet treat)

• An outdoor sauna, spa bath, and in-room spa services 

• The pleasure of stunning sunsets, tranquil surroundings, and luxury suites
  
  

Love lighthouses, history, or lobster rolls? A day trip to Portland, Maine, is totally worth it. Let us help you make the most of it—starting and ending your day at Wolf Cove Inn.

📆  Book your stay today, and let’s make your Maine day trip the best one yet.

 

Photo Credit: © agaliza from Getty Images via canva.com, © Sean Pavone from Getty Images Pro via canva.com, © rebeccafondren from Getty Images via canva.com,