10 Best Things to Do in Portland, Maine for First-Timers

If you’re planning your first trip to Portland, Maine, you’re in for a treat. This coastal city is easy to explore on foot, packed with great food, and has just the right mix of history and laid-back charm. Fall is an especially nice time to visit, with cooler temps, changing leaves, and fewer crowds than in summer.

We recently spent a few days here and loved how much there was to do without it feeling overwhelming. From lighthouses and historic homes to donuts, breweries, and waterfront views, it’s the kind of place that’s fun to explore at your own pace!

To help you plan your trip, I put together a list of the absolute best things to do in Portland, Maine, that you can’t miss as a first-timer.

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Best Things to Do in Portland, Maine

1. Explore the Old Port

If it’s your first time in Portland, start with the Old Port. This is the city’s historic downtown district, full of cobblestone streets, red brick buildings, working waterfront views, and independent shops.

You’ll find everything from cute bookstores and coffee spots to seafood restaurants and local boutiques.

The Old Port is also home to many of the best things to do in Portland, Maine, so you’ll probably end up here more than once during your trip.

It’s especially nice to wander in the morning before the crowds roll in or in the late afternoon when the golden light hits the harbor.

No real agenda needed! Just walk, browse, and stop for a snack or drink when something catches your eye.

2. Visit Portland Head Light

You can’t visit Portland without seeing its most famous lighthouse! Portland Head Light sits right on the coast in Cape Elizabeth, about a 15-minute drive from downtown.

It’s one of the most photographed lighthouses in the country, and honestly, the setting is just as good as the lighthouse itself.

It’s located inside Fort Williams Park, which has walking trails, ocean views, and food trucks in the warmer months. There’s also a small museum inside the former keeper’s house if you want to learn more about the history.

You can visit on your own or join The Real Portland Tour, which includes a stop at the lighthouse along with a few other highlights around the city.

3. Tour the Portland Museum of Art

The Portland Museum of Art is one of the top cultural attractions in the city and a must if you’re looking for what to do in Portland, Maine on a rainy or chilly day.

It’s not huge, but the collection is well-curated and includes works by American artists like Winslow Homer, Andrew Wyeth, and Georgia O’Keeffe.

The museum is located in the Arts District, just a short walk from the Old Port. It’s a nice way to spend an hour or two, especially if you enjoy a quieter, more relaxed museum experience. They also host rotating exhibitions, so there’s usually something new to check out.

Admission is free on Fridays from 4 to 8 pm, which is a great option if you’re visiting on a budget.

4. Step inside the Wadsworth-Longfellow House

Just a few blocks from the Old Port, this historic house offers a unique peek into Portland’s past. The Wadsworth-Longfellow House was the childhood home of poet Henry Wadsworth Longfellow and is the oldest standing structure on the Portland peninsula.

Inside, the rooms are filled with original furnishings, portraits, and handwritten letters from the Longfellow family.

It’s a quick but interesting stop if you’re into local history or old homes, and guided tours help bring the stories to life.

It’s one of those Portland Maine, attractions that often flies under the radar, but is absolutely worth checking out, especially if you’re already nearby.

Right next door, you’ll find Longfellow Books, an independent bookstore with a cozy vibe and great local selection. It’s the perfect spot to browse after your tour!

5. Eat your way through Portland (don’t miss the Holy Donut!)

Portland has a food scene that punches way above its size, and one of the best ways to experience it is by joining a guided food tour!

The Old Port Culinary Walking Tour includes up to seven stops with enough tastings to replace a full meal. Along the way, your guide shares stories about the city’s food culture and local favorites.

If you’d rather explore on your own, there’s no shortage of places to try. One local favorite you shouldn’t miss is The Holy Donut.

Their sweet potato donuts are made with real Maine potatoes and come in flavors like maple, cinnamon sugar, and dark chocolate sea salt. They have two locations in the city, and they often sell out, so go early if you can!

If you’re really into donuts, there’s also a dedicated walking tour called Warm Donuts, History & Hidden Gems. It includes three donut stops around the Old Port and some fun history along the way.

6. Walk around Bug Light Park

Bug Light Park is a peaceful little spot in South Portland with great views of the harbor and downtown skyline. The park is named after the small lighthouse on site, officially called Portland Breakwater Light, but everyone just calls it Bug Light.

It’s a nice place for a short walk, especially around sunset when the light hits the water and city in the distance. You’ll often see locals flying kites, walking dogs, or just hanging out on the grass.

If you’re looking for what to do in Portland, Maine that’s a bit more relaxed, this is an easy and scenic stop to add to your list.

7. Visit Victoria Mansion

If you’re looking for things to do in Portland, Maine beyond the waterfront and food scene, this historic house is a cool stop.

Victoria Mansion is just a few blocks from the Arts District and gives you a look at how fancy summer homes used to be in the 1800s.

The inside is filled with original furniture, colorful walls, and some seriously detailed ceilings. You can do a guided tour or just walk through on your own if you’re short on time.

It’s not a long visit but it’s something different and worth popping into, especially in the fall when the trees outside are turning.

8. Take a Harbor Lights and Sights Cruise

One of the most relaxing things to do in Portland is to get out on the water. The Harbor Lights and Sights Cruise gives you a front-row view of Casco Bay, nearby islands, and a few iconic lighthouses along the way.

The boat ride lasts about 90 minutes and runs seasonally from spring through fall. It’s a great way to see the coastline without having to plan a full day trip!

You’ll also learn a bit about Portland’s history and working waterfront as you cruise along. Try to grab a spot on the top deck for the best views!

9. Go brewery hopping in Portland

Portland has one of the best craft beer scenes in New England, with dozens of breweries packed into a small area. Many are clustered around the East Bayside neighborhood, which makes it easy to walk between them.

Bissell Brothers, Austin Street, and Rising Tide are great places to start. If you’re into funky or farmhouse-style brews, Oxbow is a fun one to try. Most spots have outdoor seating in the warmer months and often host food trucks or pop-ups.

If you’re working through your Portland, Maine bucket list, a brewery stop or two definitely belongs on it!

10. Climb the Portland Observatory

For one of the best views in the city, head to the Portland Observatory! This historic wooden tower sits on a hill overlooking downtown and the harbor, and you can climb to the top for a full 360-degree view.

Built in 1807, it was originally used to spot ships coming into port before the days of radio. Today it’s a small museum, and guided tours take you up through the levels with quick stops to learn about Portland’s maritime history.

The observatory is only open from late May to early October, so if you’re visiting in the fall, be sure to check the schedule before you go.

It’s a fun and easy add-on if you’re looking for what to do in Portland, Maine that includes a little history and a great photo op.

Where to Stay in Portland, Maine

Portland is compact and easy to get around, so most first-time visitors choose to stay near the Old Port or the Arts District.

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

Where to Eat in Portland, Maine

Portland has way more great restaurants than you could possibly fit into one trip! From casual takeout spots to cozy bistros and waterfront seafood joints, there’s no shortage of good food around here.

Here are a few local favorites to check out:

• Eventide Oyster Co. – Small plates and fresh oysters, often with a wait but worth it
• The Holy Donut – Famous for their sweet potato donuts, with two locations in the city
• Central Provisions – Inventive shared plates in a historic space, right in the Old Port
• Tandem Coffee + Bakery – Great coffee and baked goods in a converted gas station
• Duckfat – Casual spot known for hand-cut fries, paninis, and milkshakes