Portland, Maine (Cumberland County): 10 Unmissable Things To Do Nearby

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10 Unforgettable Things To Do Near Portland, Maine (Cumberland County Guide)

If you’re dreaming about salty ocean air, historic brick streets, and some of the best seafood in New England, Portland, Maine should be at the top of your list. This guide covers 10 amazing things to do in and around Portland, Maine (Cumberland County)—perfect for a long weekend or a full-on getaway. Whether you love food, lighthouses, or just wandering cute coastal towns, you’ll find something here you’ll want to bookmark.

1. Stroll the Historic Old Port & Waterfront

Portland’s Old Port is the heart of the city and a must-see on any Portland, Maine itinerary. Picture this: cobblestone streets, brick warehouses turned into boutiques and bars, and working fishing boats bobbing in the harbor. It’s one of those places where you start out “just walking around” and suddenly, two hours have disappeared. What to do in the Old Port:
  • Browse local shops for Maine-made goods (pottery, candles, local art).
  • Grab a lobster roll or chowder at a waterfront restaurant.
  • Stop for a local craft beer or cocktail at one of the many bars.
  • Walk down to the piers and watch the ferries and fishing boats.
If you enjoy people-watching, find a bench and just soak it all in. On summer evenings, the Old Port feels lively but still relaxed—very classic coastal New England.

2. Visit the Iconic Portland Head Light in Cape Elizabeth

About 15 minutes south of downtown Portland, in nearby Cape Elizabeth, you’ll find one of the most famous lighthouses in America: Portland Head Light. Set inside Fort Williams Park, this lighthouse looks like something straight off a postcard. Rocky cliffs, crashing waves, and that classic white tower—it’s no surprise it’s one of the top things to do near Portland, Maine. Highlights at Portland Head Light:
  • Walk the cliffside paths with sweeping ocean views.
  • Explore the old military ruins scattered around the park.
  • Visit the small museum inside the former keeper’s house (seasonal).
  • Enjoy a picnic on the grass or grab food from one of the park’s food trucks.
If you’re into photography, try to get here early in the morning or close to sunset. The light on the water is unreal.

3. Eat Your Way Through Portland’s Food Scene

For a small city, Portland, Maine has a huge reputation for food. Some people come here just to eat—and honestly, that’s not a bad plan. You’ll find:
  • Fresh-off-the-boat lobster rolls (hot with butter or cold with mayo).
  • Oysters, clams, and all kinds of local seafood.
  • Farm-to-table restaurants using ingredients from Maine farms.
  • Creative bakeries, donut shops, and coffee roasters.
If you’re overwhelmed by choices, consider:
  • Doing a food tour – Several local companies offer walking food tours around the Old Port, which is a fun way to learn about the city while tasting your way through it.
  • Popping into small spots – Sometimes the best meals are at the places you stumble across while exploring.
Tip: Popular restaurants can book up fast, especially in summer and fall. If there’s a spot you really want to try, make a reservation ahead of time.

4. Take a Ferry to the Casco Bay Islands

Looking for a quick escape from the city without a long drive? Head to the Casco Bay Lines terminal on the Portland waterfront and catch a ferry to one of the nearby islands. Popular choices include:
  • Peaks Island – Just a short 15–20 minute ride. Rent a bike or golf cart, circle the island (about 4 miles around), and enjoy quiet beaches and ocean views.
  • Great Diamond Island – A bit quieter, with historic buildings and peaceful walking paths.
  • Long Island and more – Each island has its own vibe and pace.
Why this is a must-do:
  • You get beautiful views of the Portland skyline and harbor.
  • It’s an easy way to experience island life without a long trip.
  • Great for families, couples, or solo travelers who want a calm day.
Pack a light jacket, even in summer—ocean breezes can feel cooler than you expect once you’re out on the water.

5. Explore the Eastern Promenade & Back Cove Trails

If you like to walk, run, or bike, you’ll love the Eastern PromenadeCasco Bay. There’s a paved path, a small beach, picnic areas, and play spaces. Things to do on the Eastern Prom:
  • Walk or bike along the water and enjoy constant views of the bay.
  • Spread out a blanket and watch boats and ferries come and go.
  • Kayak or paddleboard from the small beach area (rentals are often available nearby in season).
For a different kind of waterfront walk, check out the Back Cove Trail, a mostly flat loop of about 3.5 miles around a tidal basin. It’s popular with runners, dog walkers, and casual strollers. If you’ve been eating your way through the city, these trails are a great way to balance that out a bit.

6. Discover Art & History: Portland Museum of Art & Wadsworth-Longfellow House

On a rainy day—or if you’re just in the mood for something indoors—Portland has a surprisingly strong arts and history scene for a city its size. Portland Museum of Art:
  • Located downtown near Congress Square.
  • Features American, European, and contemporary art.
  • Includes works by famous artists as well as local Maine talent.
Just a short walk away, you can also tour the Wadsworth-Longfellow House, childhood home of poet Henry Wadsworth Longfellow. It’s one of the oldest brick homes in Portland and gives a nice glimpse into 19th-century life. If you’re traveling with kids or teens, this can be a nice way to mix culture into your Portland, Maine trip without it feeling like a school field trip.

7. Visit Freeport for Shopping & Coastal Walks

About 20 minutes north of Portland, still in Cumberland County, you’ll find Freeport, Maine—best known for being the home of L.L.Bean. Why go to Freeport?
  • Shopping – Outlet stores, local boutiques, and the famous L.L.Bean flagship store, which is open 24 hours a day.
  • Outdoor fun – Just a short drive from Freeport’s center is Wolfe’s Neck Woods State Park with easy trails through the woods and beautiful ocean views.
If you like the idea of browsing gear and then actually going out to use it, Freeport is your place. You can spend the morning walking trails and the afternoon shopping, or vice versa. Parking is generally easy here, and it makes a great half-day trip from Portland.

8. Enjoy Breweries & Distilleries Around Portland

If you’re a craft beer fan, Portland, Maine is going to feel like a playground. The city and surrounding Cumberland County area are packed with breweries, many with taprooms and outdoor seating. Here’s what to expect:
  • A wide mix of styles—IPAs, stouts, sours, lagers, and more.
  • Laid-back taprooms that welcome both locals and visitors.
  • Food trucks parked outside many breweries, especially in warmer months.
Not into beer? No problem. There are also local distilleries and cideries around Portland offering tastings of gin, rum, whiskey, hard cider, and more. If you’d rather not drive, consider:
  • Joining a guided brewery tour.
  • Planning a mini “brewery crawl” using rideshare or the local bus to get around safely.
Always remember to pace yourself and drink plenty of water—especially if you’re walking a lot during the day.

9. Take a Day Trip to Coastal Towns: Brunswick & Harpswell

If you have a car, it’s worth exploring a bit more of Cumberland County beyond Portland and Freeport. Two nearby coastal areas to consider: Brunswick, Maine:
  • About 35–40 minutes from Portland.
  • Home to Bowdoin College, giving the town a friendly, college-town feel.
  • Offers galleries, restaurants, and a walkable downtown.
Harpswell, Maine (nearby):
  • Full of classic Maine coastal scenery—peninsulas, islands, and narrow roads with water on both sides.
  • Great for scenic drives, photo stops, and peaceful walks.
These spots feel a little quieter and slower than Portland. If you’re craving that “small fishing village” energy, this is where you’ll start to feel it.

10. Hit the Beach at Crescent Beach or Scarborough Beach

Yes, Maine is known for rocky shores—but there are also some wonderful sandy beaches within a short drive of Portland. Two local favorites:
  • Crescent Beach State Park (Cape Elizabeth) – A wide, sandy beach with gentle waves and views of distant islands. Great for families and casual swimmers.
  • Scarborough Beach State Park (Scarborough, also in Cumberland County) – A little wilder, with stronger surf and long stretches of sand.
Water temps in Maine are on the colder side, even in summer, but on a hot July or August day, that can feel pretty refreshing. Don’t forget:
  • Sunscreen (the coastal breeze can be sneaky).
  • A light layer—weather can change quickly by the ocean.
  • A small cooler for drinks and snacks if permitted.
These beaches offer a nice change of pace from downtown Portland and round out a classic Maine coastal getaway.

Planning Your Portland, Maine Trip: Final Tips

To make the most of your visit to Portland and Cumberland County, Maine, keep these quick tips in mind:
  • Best time to go: Late spring through fall (May–October) offers the best mix of weather, open businesses, and outdoor fun.
  • Getting around: Downtown Portland is very walkable. For lighthouses, beaches, and nearby towns, having a car makes things easier.
  • What to pack: Layers, comfortable walking shoes, a light rain jacket, and something warm for cool evenings—even in summer.
Whether you’re here for the food, the views, or just a break by the water, Portland, Maine has a way of getting under your skin in the best possible way. Many people leave already planning their next trip back.

What Would You Add to This Portland, Maine Bucket List?

Have you been to Portland or Cumberland County, Maine before? Did I miss one of your favorite things to do near Portland—maybe a hidden park, a local café, or a must-try lobster roll spot? I’d love to hear from you:
  • Drop your favorite Portland, Maine activities in the comments.
  • Share your best local tips for first-time visitors.
  • Tell us: which of these 10 things would you do first?
If you found this guide helpful, please share it with friends or family who are planning a trip to Maine. It might be the gentle nudge they need to finally book that coastal vacation.
Location: Georgetown, IN, USA

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