One Day in Portland, Maine: The Best Day Trip Guide

Planning to spend one day in Portland, Maine? This small coastal city has a lot to offer, from historic neighborhoods and waterfront views to local food spots and iconic lighthouses.

Whether you’re coming up for the day or fitting it into a New England road trip, this one day Portland itinerary covers all the highlights.

I’ll walk you through exactly how to spend one day in Portland, with a mix of walkable city sights, a scenic lighthouse loop, and plenty of great food along the way!

Disclaimer: Some of the links in this post are affiliate links, which means I may earn a small commission if you make a purchase, at no extra cost to you.

How to Spend One Day in Portland, Maine

Holy Donut

Let’s start your one day in Portland, Maine the right way: with donuts!

Holy Donut is a Portland classic, and for good reason. They make their donuts with Maine potatoes, which might sound strange at first, but gives them a really great texture. Soft and dense in the best way!

Flavors change often, but you’ll usually find blueberry, maple bacon, and dark chocolate sea salt. The Exchange Street location is right downtown and gets busy fast, so it’s best to go early while everything’s fresh.

Even if you’ve already had breakfast, it’s worth saving some space for these donuts!

Walk through the Old Port

After breakfast, take some time to wander through the Old Port. This is the heart of downtown Portland, and one of the best areas to explore on foot. Cobblestone streets, historic brick buildings, working wharves, and a mix of local shops give it a lot of charm without feeling too polished.

Most stores open around 10 am, but even if you’re out earlier, it’s still a great place to walk around and soak in the atmosphere. Pop into a coffee shop, check out a local bookstore, or just enjoy the harbor views from the end of one of the piers.

If you’re wondering what to do in Portland, Maine in one day, this is the place to start. It’s walkable, easy to navigate, and gives you a great first impression of the city!

Portland Observatory

Next up is the Portland Observatory, one of the more unique historic spots in the city. It’s an old wooden signal tower that was used to spot ships coming into the harbor back in the 1800s.

These days, you can climb to the top for panoramic views over the city and Casco Bay and if the weather is great, I really recommend doing it!

It’s only open seasonally from late May through early October, and hours vary depending on the day, so be sure to check ahead if it’s something you really want to do.

If it’s closed, it’s still worth walking up Munjoy Hill to see it from the outside and enjoy the neighborhood views.

It fits really well into a Portland, Maine one day itinerary since it’s close to the Old Port and only takes about 30 to 45 minutes, depending on how long you hang out at the top.

Downtown Portland

After the observatory, take a walk down Congress Street as you head back toward the center of town.

This stretch is full of landmarks worth noticing along the way. You’ll pass the Cathedral of the Immaculate Conception, Lincoln Park, Portland City Hall, and Merrill Auditorium, all within a few blocks of each other.

It’s a nice way to see a bit more of the city’s architecture without adding extra stops.

Eventually, you’ll reach Monument Square, one of Portland’s main public spaces. It’s not huge, but it’s a central gathering spot with local shops and cafés nearby.

Right next to the square, you’ll have two optional stops. The Wadsworth-Longfellow House is just off the square and offers a quick dive into Portland’s history.

It’s the poet’s childhood home and one of the oldest buildings downtown. Tours are seasonal, but even if it’s closed, there’s a small garden you can peek into from the sidewalk.

If you’d rather keep things low-key, Longfellow Books is right across the way. It’s a cozy indie bookstore with a good Maine section and a nice spot to browse before lunch.

Portland Museum of Art or Victoria Mansion

Before lunch, squeeze in one more stop, either the Portland Museum of Art or Victoria Mansion, depending on what you’re more into.

The Portland Museum of Art is right downtown and easy to visit without needing much time. It has a solid mix of American and European works, along with a strong focus on New England artists.

The layout is clean and manageable, so you can see quite a bit in under an hour if you’re moving at a steady pace.

If you’d rather visit a historic home, Victoria Mansion is just a few blocks away. It’s a beautifully preserved 19th-century house with ornate interiors and original furnishings.

The outside is worth a look too, especially if you’re visiting off-season or don’t have time for a full tour.

Both options give you a quick dose of culture and fit nicely into a plan for seeing Portland, Maine in a day.

Lunch in the Old Port

If you only have one day in Portland, Maine, this is the time to try a lobster roll! There are plenty of great spots downtown, but three casual favorites stand out.

Portland Lobster Company has a laid-back vibe right on the water, with picnic tables, live music in the warmer months, and classic lobster rolls served with fries.

Highroller Lobster Co. is a fun, slightly quirky spot that puts their own twist on things, with tons of topping options and a diner-style setup.

And if you’re after something a bit more polished but still casual, Luke’s Lobster on Portland Pier has a great location with water views and reliably fresh rolls.

All three are within walking distance of the waterfront and make for an easy lunch stop before you head out for an afternoon of lighthouse hopping.

Portland Head Light & Fort Williams Park

After lunch, head out of downtown for the most scenic part of your Portland, Maine one day itinerary. A quick drive or rideshare will take you to Cape Elizabeth, home to Portland Head Light!

This is Maine’s most photographed lighthouse, and it’s easy to see why. The setting is beautiful, with rocky cliffs, crashing waves, and wide ocean views.

Fort Williams Park has plenty of walking paths and a few old military structures to explore while you’re there. If you didn’t grab lunch earlier, there are often food trucks parked nearby with lobster rolls and snacks.

You won’t need more than an hour here unless you want to stay and relax for a while. It’s a straightforward stop and a must for first-time visitors.

If you’re not keen on driving, consider joining The Real Portland Tour! The tour starts downtown and includes Portland Head Light and other local lighthouses. It runs with a small group and comes with insights from a knowledgeable guide.

Spring Point Ledge Lighthouse

Next up is Spring Point, just a short drive from Portland Head Light. What makes this lighthouse different is that you can actually walk right out to it!

A granite breakwater stretches into the harbor, and if you’re up for the uneven stones, it leads you straight to the base of the light.

The views are great from out on the breakwater, and it’s usually less crowded than Portland Head. There’s also a small beach nearby and the remains of Fort Preble if you feel like exploring a bit more.

This stop doesn’t take long, so it’s an easy addition to your afternoon without feeling rushed.

Bug Light Park

Wrap up your lighthouse loop at Bug Light Park, just a few minutes from Spring Point.

The lighthouse here is smaller than the others, but the setting is peaceful with a wide-open lawn, walking paths, and great views back toward the Portland skyline.

The official name is Portland Breakwater Light, but most people just call it Bug Light. It’s easy to access and doesn’t take much time, so it’s a nice, low-effort stop to include during your 1 day in Portland, Maine.

If the weather’s nice, this is also a great place to sit for a few minutes before heading back into the city.

Dinner in the Old Port

After a full afternoon by the water, head back into town for dinner. The Old Port is packed with great spots, and it’s a nice area to finish off your one day Portland, Maine itinerary.

If you’re still craving seafood, Boone’s Fish House & Oyster Room is a solid pick. It’s right on the water and has outdoor seating when the weather’s good.

For something more refined, Fore Street serves up wood-fired dishes with a focus on local ingredients. Both are walkable from pretty much anywhere downtown.

If you’re in the mood for something more casual, you’ll find plenty of pubs, pizza, and quick bites around Exchange and Commercial Streets, too.

Where to Stay in Portland, Maine

Portland is compact and easy to get around. I recommend staying either in the Old Port or Downtown Portland.

These areas put you within walking distance of shops, restaurants, the working waterfront, and most of the city’s top sights.

Here are a few great options to consider:

• Canopy by Hilton Portland Waterfront – Modern, upscale option with harbor views and a great location near the Old Port
• The Press Hotel – Stylish boutique hotel in a former newspaper building, right near City Hall
• Hampton Inn Portland Downtown Waterfront – Comfortable chain hotel just steps from the harbor and Old Port
• Inn at St. John – Budget-friendly with a bit of historic charm, located just outside downtown