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Things to do in Portland Maine

Portland Head Light

Our family spent a few days in Maine in order to find out if it would be a good future home for our family. We stayed in a wonderful hotel in Portland, Maine and ventured out each morning to discover everything we could about the area and chatting with local Mainers. 

The Good thing is, there are so many fun things to do in Portland Maine! It was an absolutely dreamy journey along rocky coastlines, beautiful autumn leaf displays, and some of the most friendly people I have ever met. 

Our Family also traveled to Boston, Massachusetts during this East coast road trip! Read more here. 

Nestled along the rocky coastline of Casco Bay, Portland, Maine, is a quintessential New England destination that blends rich history, vibrant culture, and stunning natural beauty. Whether you’re a history buff, foodie, outdoor adventurer, or art enthusiast, Portland has something to offer everyone.

Known for its cobblestone streets, brick buildings, and working waterfront, this charming city invites visitors to explore its Old Port, shop at local boutiques, and enjoy fresh lobster straight from the sea. From iconic lighthouses and scenic parks to museums and craft breweries, Portland is packed with unforgettable experiences.

Thanks to its easy access from Boston’s North Station and the Portland Transportation Center, Portland is a convenient and accessible getaway. Whether you’re planning a quick weekend trip or a more extended vacation, this city is the perfect spot to relax, dine, and discover.

Read on to learn about the top 10 things to do in Portland Maine, and make the most of your visit to this coastal, New England gem.

Explore the Old Port and Downtown Portland

Portland’s Old Port and downtown areas are brimming with character, making them a must-visit for anyone looking to experience the city’s charm. The cobblestone streets and brick buildings create a picturesque setting for exploring local shops, dining at renowned restaurants, and enjoying lively bars.

Things to Do:

  • Stroll along Commercial Street, the heart of the working waterfront, where fishing boats dock and seafood markets bustle.
  • Sample local delicacies at food trucks or sit down for lobster rolls and pizza at waterfront restaurants.
  • Visit breweries for craft beer tastings and enjoy dessert shops offering sweet treats.


    Pro Tip: Many attractions in this area are within walking distance, and free parking is available near the Casco Bay Bridge or on side streets for easy access to downtown fun. The close vicinity of everything makes it easier to do a lot of things in Portland Maine. 

Visit the Iconic Portland Head Light

things to do in Portland maine
One of our littles watching the waves at the Portland Head Light.

No trip to Portland, Maine, is complete without visiting the Portland Head Light, one of the most photographed lighthouses in the United States. This historic site combines breathtaking scenery with a rich history in Cape Elizabeth at Fort Williams Park.

Things to Do at Portland Head Light:

  • Walk along the cliff walk, which offers panoramic views of Casco Bay and the rocky coastline.
  • Explore Fort Williams Park’s open spaces, picnic areas, and scenic walking trails.
  • Capture stunning photos of the lighthouse, especially during sunset or the summer months when the weather is perfect.
  • Learn about the site’s maritime history at the small onsite museum inside the former keeper’s house.

Travel Tip: Bring a blanket and snacks for a picnic with a view, or grab a bite from nearby food trucks. Parking is available at Fort Williams Park, making it a stress-free stop that’s great for kids to run around and get their wiggles out.

things to do in Portland maine 1

Take a Ferry to the Casco Bay Islands

The Casco Bay Islands provide a peaceful retreat just minutes from downtown Portland. Whether you’re looking for outdoor activities, scenic views, or quiet exploration, these islands are easily accessible via ferry rides.

Highlights:

  • Peaks Island – A personal favorite for biking, boutique shopping, and waterfront dining. It’s a great place to relax and soak up the views.
  • Enjoy kayaking, hiking, and beachcombing on the other islands like Great Diamond Island and Long Island.
  • Take in the sea breeze and views of lighthouses and boats during the ferry ride.

Tips for Travelers:

  • Ferry services depart from the terminal near Commercial Street and offer multiple departures daily, especially during summer.
  • Plan a day trip or spend the night in one of the island’s inns or vacation rentals.
  • Be sure to check ferry schedules in advance, and bring bikes or walking shoes to explore at your own pace.

Indulge in Portland's Food Scene

things to do in Portland maine
Jenni thrilled to finally be trying Holy Donuts!

Portland’s food scene is a paradise for food lovers. This is one thing about Maine that our family of foodies loves!! From fresh seafood to international flavors, there’s something for everyone. One of my favorite things to do in Portland Maine is to eat delicious food! Portland has earned a reputation as one of the best food cities in New England, offering culinary delights for every palate.

What to Eat:

things to do in Portland maine 2
Lobster rolls at the Portland Lobster Company in Portland, Maine.

Seafood Specialties: At waterfront restaurants, enjoy fresh lobster rolls at the Portland Lobster Company, clam chowder, and oysters. Many eateries serve seafood straight from the boat, ensuring top quality and flavor.

Comfort Foods: Try wood-fired pizza, gourmet burgers, and farm-to-table dishes in downtown Portland. Restaurants along Congress Street and Commercial Street offer diverse menus perfect for any craving.

things to do in Portland maine 1
Our family's order of Holy Donuts!

Sweet Treats: Grab dessert at local bakeries and ice cream shops. Be sure to try Portland’s famous Holy Donut, which is made with Maine potatoes for a unique flavor. Food trucks scattered around the city offer pastries and creative snacks.

Breweries and Beverages: Portland is home to an impressive craft beer scene. Visit breweries to taste locally made beers, ciders, and kombucha. Popular spots include Allagash Brewing Company and Rising Tide Brewing.

Pro Tip: Many restaurants have outdoor seating, perfect for enjoying the sea breeze during the summer months. Make reservations in advance, especially during peak tourist seasons, to secure a table at popular dining spots. For travelers with dietary restrictions, Portland also offers plenty of vegetarian, vegan, and gluten-free options.

Explore the Portland Museum of Art

The Portland Museum of Art, located in the heart of downtown Portland on Congress Street, is a cultural gem that art and history enthusiasts won’t want to miss. This museum is the oldest and largest public art institution in Maine, showcasing a diverse collection of works from American and European masters and contemporary artists.

What to Expect:

Diverse Art Collections: The museum features an impressive range of exhibits, including sculptures, paintings, and photography. Explore works spanning centuries, from classical European pieces to modern installations.

Renowned Artists: Admire masterpieces by celebrated artists such as Winslow Homer, Andrew Wyeth, Claude Monet, and Mary Cassatt.

Interactive Experiences: Participate in guided tours, rotating special exhibits, and hands-on workshops designed for visitors of all ages.

Family-Friendly Activities: The museum offers engaging programs for kids and families, including art-making activities and scavenger hunts.

Outdoor Spaces: Relax in the beautifully designed sculpture garden, a serene spot to unwind and reflect on the artwork.

Pro Tip: Check the museum’s website for free admission days, discounts, and upcoming events. If you’re visiting during the summer, look out for seasonal outdoor programs and art fairs nearby. The museum is also within walking distance of many restaurants, making it a perfect stop before or after lunch.

Relax at the Eastern Promenade and Casco Bay Bridge

For breathtaking views and outdoor relaxation, the Eastern Promenade and Casco Bay Bridge are must-visit destinations in Portland, Maine. Located along the waterfront, this scenic area offers recreational activities and stunning Casco Bay and the Fore River vistas.

Things to Do:

Walking and Biking Trails: Take advantage of the well-maintained trails perfect for walking, jogging, or biking while soaking in the coastal scenery.

Picnicking and Relaxing: Enjoy a picnic at one of the park’s many green spaces, with panoramic views of sailboats and the sparkling waters of Casco Bay.

Sunset and Wildlife Viewing: Capture stunning sunset views over the Fore River, and watch for seabirds and marine wildlife along the shore.

Water Activities: Rent a kayak or paddleboard to explore the coastline or simply watch boats pass under the Casco Bay Bridge.

Playgrounds and Open Fields: Families will love the playgrounds and wide-open fields for outdoor games and activities.

Pro Tip: The Eastern Promenade offers free parking and is easily accessible from downtown Portland. Visit during summer to enjoy seasonal food trucks and pop-up vendors selling snacks and refreshments.

Visit Fort Gorges and the Portland Observatory

History and adventure await at Fort Gorges and the Portland Observatory, two iconic landmarks that showcase Portland’s maritime past and architectural heritage. These sites provide fascinating insights into Portland’s history and offer some of the best views in the city.

Fort Gorges:

Boat Tours and Kayaking: Accessible only by boat, Fort Gorges is a hidden gem sitting on Hog Island Ledge in Casco Bay. Built during the Civil War, it was designed as a coastal defense fortification but was never fully armed. Today, it’s an off-the-beaten-path adventure for history buffs and explorers.

Explore the Ruins: Wander through the abandoned granite fort and take in the architecture, which has remained largely untouched since the 19th century. Interpretive signage provides insights into the fort’s history and construction.

Picnic and Photography Opportunities: Bring a packed lunch and enjoy a peaceful picnic while surrounded by breathtaking views of the bay. The fort’s remote location also makes it ideal for photography enthusiasts looking to capture stunning coastal shots.

Wildlife Spotting: The area around the fort is home to seabirds and other wildlife, making it an excellent spot for birdwatching and nature photography.

Portland Observatory:

Climb to the Top: Standing at 86 feet tall, the Portland Observatory is the last surviving maritime signal tower in the United States. Built in 1807, it provided a vantage point for shipowners to monitor their vessels entering the harbor.

Panoramic Views: After climbing 103 steps to the top, visitors are rewarded with stunning 360-degree views of Portland, Casco Bay, and the surrounding islands.

Guided Tours: Knowledgeable guides share fascinating stories about Portland’s maritime history, the observatory’s role in shipping, and its architectural significance.

Interactive Exhibits: Learn about the tools and techniques early signalmen use to communicate with incoming ships. The exhibits make it an engaging experience for both adults and kids.

Restored Landmark: Admire the restored 19th-century structure, which symbolizes Portland’s seafaring heritage and resilience.

Pro Tip: Plan your visit during the summer months when Fort Gorges tours and Observatory hours are more frequent. Boat rentals and guided tours for Fort Gorges are popular, so book in advance to secure your spot. Don’t forget to bring comfortable shoes and a camera to capture the views!

Discover Victoria Mansion and Historic Buildings

Victoria Mansion, Portland, Maine, USA.
Victoria Mansion, Portland, Maine, USA.

Step back in time with a visit to Victoria Mansion, one of Portland’s architectural treasures, and explore the city’s other historic buildings. Known as the Morse-Libby House, Victoria Mansion is a stunning example of 19th-century Italianate architecture and a must-see for history and design enthusiasts.

What to See:

19th-Century Furnishings and Intricate Decor: The mansion’s interior remains remarkably preserved, showcasing original furnishings, opulent textiles, and elaborate woodwork. From hand-painted ceilings to gilded mirrors, every detail reflects the grandeur of the mid-1800s.

Guided Tours Offering Insights into Portland’s History: Knowledgeable guides lead visitors through the mansion, sharing stories about its original owners, Ruggles and Olive Morse, and the home’s role in Portland’s history.

Architecture and Design Details: Admire the mansion’s exterior with its impressive columns, ornate trim, and stately entrance. The design represents one of the finest examples of pre-Civil War architecture in the United States.

Other Historic Buildings to Explore:

Wadsworth-Longfellow House: Visit the childhood home of the famous poet Henry Wadsworth Longfellow, featuring period furnishings and gardens. This National Historic Landmark provides insights into early 19th-century life.

First Parish Church: Dating back to 1825, this historic church features Federal-style architecture and beautifully preserved stained-glass windows.

Custom House: Located in the Old Port district, this granite building showcases 19th-century Renaissance Revival architecture and reflects Portland’s maritime and trade history.

Eastern Cemetery: Explore Portland’s oldest historic burial ground, established in 1668. This site offers fascinating insights into the city’s earliest settlers and Revolutionary War heroes.

Pro Tip: Many of Portland’s historic buildings are within walking distance of each other, making planning a day of exploration easy. Check seasonal hours and tour schedules in advance, as some sites offer limited access during off-peak months.

Shop and Stroll Through Local Markets and Boutiques

things to do in Portland maine 6

Portland, Maine, is a shopper’s paradise, blending local charm with unique finds. Whether you’re looking for handmade crafts, art, or locally sourced food, the city’s markets and boutiques have something for every visitor.

Highlights:

farmers market in portland maine
Apples for sale at the Portland Farmers Market.

Portland Farmers’ Market: Held in Deering Oaks Park, this market offers seasonal produce, baked goods, and artisanal products. It’s the perfect spot to pick up farm-fresh ingredients or sample Maine-made treats.

Craft Fairs and Pop-Up Markets: Portland frequently hosts markets featuring handmade jewelry, ceramics, textiles, and artwork created by local artists.

Boutiques and Specialty Stores: Wander the cobblestone streets of the Old Port district, where boutique shops sell everything from books and clothing to home décor and souvenirs. Many stores feature products crafted by Maine artisans.

things to do in maine
A treasured purchase! We brought home Maine Maple Syrup to bring a little bit of Maine home with us.

Foodie Finds: Stop by gourmet shops offering locally roasted coffee, fresh seafood, and artisanal cheeses. Don’t forget to pick up some wild blueberry jam or Maine Syrup—Maine specialties!

Pro Tip: Many shops and markets are within walking distance of key attractions, and free parking is often available nearby. Arrive early to beat the crowds, especially during summer and holiday weekends.

Start Planning a Visit to Portland, Maine!

There are so many great things to do in Portland Maine! It offers an unforgettable experience for travelers seeking history, culture, and coastal charm. From exploring historic buildings and visiting the iconic Portland Head Light to relaxing by Casco Bay and shopping for unique treasures, this city has something for everyone.

Whether you enjoy a lobster roll by the waterfront, admire art at the Portland Museum of Art, or discover local crafts at the farmers’ market, Portland will leave a lasting impression.

Plan your trip today and visit Portland to experience the very best of this New England gem!

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Jenni Sekine

Mother of Dragons

Hey there! I'm Jenni, a homeschooling, home birthing, and home growing mama of four little dragons, and I run Dragon's Hearth Homestead with my husband, Bryan Sekine. We are all about teaching others about the things we are passionate about. Come learn with us!

🌿 home grown 🌿 🍁 homeschool 🍁 🐓 home raised 🐇 🚗 travel ✈️

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