15 Best Things to Do in Portland (Maine)

Imagine a coastal gem where historic charm meets modern vibrancy, where the scent of the salty Atlantic air mingles with the aroma of freshly brewed coffee and gourmet seafood. Welcome to Portland, Maine, a city that consistently captivates visitors with its unique blend of rugged beauty, culinary innovation, and artistic spirit. Nestled on a peninsula jutting into Casco Bay, Portland offers an authentic New England experience, from its bustling working waterfront to its quaint cobblestone streets.

You’ll discover lighthouses standing sentinel against dramatic seascapes, world-class breweries crafting unique flavors, and a thriving arts scene that buzzes with creativity. This guide will take you through the 15 absolute best things to do in Portland, ensuring your trip is filled with unforgettable moments and practical insights. The best time to visit Portland is late spring through early fall (May to October), when the weather is pleasant, and all attractions are in full swing, though a crisp autumn visit offers stunning foliage. Get ready to explore a city that truly has it all!

The Old Port

Stepping into the Old Port is like walking onto a postcard. This historic waterfront district is the vibrant heart of Portland, where cobblestone streets wind past beautifully preserved 19th-century brick buildings. What makes it truly special is its seamless blend of working fishing docks with trendy boutiques, award-winning restaurants, and lively bars.

You can spend hours simply wandering, soaking in the atmosphere, watching lobster boats unload their catch, or browsing unique shops offering everything from Maine-themed souvenirs to high-end fashion. The Old Port buzzes with energy day and night, making it perfect for a leisurely afternoon stroll, a romantic dinner, or an evening of live music. It’s a place where history feels alive, and every corner offers a new discovery, from hidden alleys to picturesque views of the harbor. This area is ideal for all types of travelers, whether you’re a solo explorer seeking charm, a couple on a romantic getaway, or a family looking for a lively place to dine and explore.

The Portland Museum of Art

The Portland Museum of Art (PMA) stands as a cultural beacon in the heart of the city, offering a surprising depth of artistic exploration for a city its size. What makes the PMA unique is its diverse collection, spanning from American art – with a strong emphasis on Maine artists like Winslow Homer and the Wyeths – to European masters, contemporary works, and photography. You can expect to wander through beautifully curated galleries, encountering pieces that provoke thought and inspire awe.

The museum also hosts rotating exhibitions that bring world-class art to Portland, ensuring there’s always something new to discover. The building itself is an architectural marvel, blending historic structures with modern additions. It’s a peaceful retreat from the bustling city, perfect for art lovers, curious minds, and anyone seeking a moment of quiet reflection. Families can also find engaging activities and educational programs.

The Allagash Brewery

For beer enthusiasts and curious visitors alike, a trip to the Allagash Brewery is a must. This isn’t just any brewery; Allagash is renowned for its Belgian-inspired beers, particularly its flagship Allagash White, which has garnered national acclaim. What makes a visit here unique is the opportunity to delve into their brewing process through informative tours, followed by generous tastings in their welcoming tasting room.

You’ll learn about their commitment to quality ingredients, traditional brewing methods, and innovative approaches. Expect to sample a variety of their core beers, seasonal releases, and even experimental brews not widely available elsewhere. The atmosphere is laid-back and friendly, making it a fantastic spot for groups of friends, couples, or solo travelers looking to expand their palate. It’s an educational and delicious experience that showcases Portland’s thriving craft beer scene.

The Peaks Island

Escape the mainland bustle with a ferry ride to Peaks Island, a charming island community just a short distance from Portland. What makes Peaks Island special is its quintessential New England island vibe – think rocky shores, quaint cottages, and a slower pace of life. You can expect to explore the island by foot, bicycle, or golf cart (rentals available near the ferry dock).

Discover hidden coves, enjoy panoramic ocean views, and visit the unique Umbrella Cover Museum. The island offers a refreshing change of scenery and a chance to truly unwind. It’s perfect for families looking for an outdoor adventure, couples seeking a romantic escape, or solo travelers desiring tranquility and natural beauty. The scenic ferry ride itself is part of the experience, offering stunning views of Portland’s skyline and Casco Bay.

The Eastern Promenade

The Eastern Promenade, affectionately known as “the Eastern Prom,” is Portland’s beloved urban oasis, offering breathtaking views and ample recreational opportunities. What makes it unique is its elevated position along the coastline, providing sweeping panoramas of Casco Bay, its islands, and the working waterfront. You can expect to walk, jog, or bike along the scenic paved path that stretches for miles, offering continuous stunning vistas.

There are also grassy areas perfect for picnics, a public beach (East End Beach), and even a historic narrow-gauge railroad. It’s a vibrant spot where locals and tourists converge to enjoy the outdoors, watch the sunrise or sunset, or simply relax with a book. This free attraction is perfect for everyone – families with kids, couples seeking a romantic stroll, solo adventurers, and dog walkers.

The Casco Bay Lines & The Mail Boat Tour

The Casco Bay Lines are more than just a ferry service; they are your gateway to the islands of Casco Bay and an experience in themselves. What makes them special is the opportunity to take the iconic Mail Boat Tour, a truly unique journey that delivers mail and supplies to the year-round island communities. You can expect a multi-hour cruise that offers an intimate look at island life, showcasing beautiful coastal scenery, charming island homes, and potentially wildlife sightings.

It’s a working boat, so you’ll witness the unique process of delivering goods to remote docks. This tour is perfect for those who love leisurely boat rides, appreciate local culture, and want to see more of Maine’s stunning coastline beyond Portland’s immediate shores. It’s a relaxing and informative way to spend a few hours on the water.

The Historic House Museum – Victoria Mansion

Step back in time at the Victoria Mansion, also known as the Morse-Libby House, one of America’s finest examples of pre-Civil War Italianate architecture. What makes this historic house museum truly unique is its remarkably preserved original interiors, boasting lavish furnishings, ornate plasterwork, and stunning frescoes that transport you to the Victorian era. You can expect a guided tour that delves into the lives of its original owners, the craftsmanship of the period, and the social history of 19th-century Portland.

Every room is a masterpiece, offering intricate details and stories. It’s a fascinating experience for history buffs, architecture enthusiasts, and anyone curious about the opulent lifestyles of America’s past. The mansion provides a rare glimpse into a bygone era, making it a truly immersive historical journey.

The Portland Observatory

The Portland Observatory stands as the last remaining maritime signal tower in the United States, offering a unique historical perspective and unparalleled panoramic views of Portland and its harbor. What makes it special is its 1807 origins, built to communicate with incoming ships before they reached the port. You can expect a guided tour that shares fascinating stories of maritime communication, the city’s seafaring past, and the lives of the signal masters.

As you ascend the tower, you’ll learn about its ingenious design and purpose. The reward at the top is a spectacular 360-degree vista, encompassing the city skyline, Casco Bay, its islands, and distant lighthouses. It’s an ideal spot for history enthusiasts, photographers, and anyone seeking the best elevated views of Portland.

The Bug Light Park

Bug Light Park, officially known as Fort Preble Park, is home to the charming Portland Breakwater Light, affectionately dubbed “Bug Light” due to its diminutive size and resemblance to a Greek temple. What makes this park special is its picturesque setting on a small peninsula, offering stunning views of Portland Harbor and the city skyline across the water.

You can expect to stroll along the paved path, enjoy a picnic on the grassy lawns, and of course, admire the unique, classical design of the lighthouse. It’s a popular spot for photographers, families, and anyone looking for a peaceful escape with beautiful coastal scenery. The short breakwater leading to the light is perfect for a leisurely walk, making it an easy and delightful stop on your Portland itinerary.

The Portland Head Light

No visit to Portland, Maine, is complete without seeing the iconic Portland Head Light, Maine’s oldest and most photographed lighthouse, standing majestically at the entrance to Portland Harbor. What makes it truly special is its dramatic setting atop rugged cliffs, with crashing waves (or calm waters, depending on the day) providing a constantly evolving backdrop.

You can expect to explore Fort Williams Park, which surrounds the lighthouse, offering miles of scenic walking trails, rocky beaches, and open fields perfect for picnicking. The lighthouse itself is a beacon of maritime history, and while you can’t go inside the tower, the former keepers’ house now hosts a small museum and gift shop. It’s an essential stop for photographers, history enthusiasts, families, and anyone seeking that quintessential Maine coastal experience.

The Commercial Street

Commercial Street is the bustling artery of Portland’s Old Port, a lively thoroughfare that encapsulates the city’s working waterfront heritage and modern vibrancy. What makes it special is its constant energy, where you can witness lobster boats unloading their daily catch just steps away from some of the city’s finest seafood restaurants and unique shops.

You can expect to stroll along the historic wharves, browse a diverse array of boutiques, art galleries, and souvenir shops, or simply enjoy a coffee while watching the harbor activity. The street is lined with historic brick buildings and offers direct access to various boat tours and ferry services. It’s a dynamic area perfect for people-watching, shopping, dining, and experiencing the authentic maritime spirit of Portland.

The Spring Point Ledge Lighthouse

Just across the harbor from Portland, in South Portland, lies the Spring Point Ledge Lighthouse, a unique “sparkplug” style lighthouse connected to the mainland by a long granite breakwater. What makes it special is the opportunity to walk directly out to the lighthouse on the impressive stone breakwater, offering a truly immersive coastal experience. You can expect to feel the ocean breeze, watch boats pass by, and enjoy uninterrupted views of Casco Bay and the Portland skyline.

The walk out is invigorating, and the lighthouse itself, though small, is charming and photogenic. It’s a perfect spot for a leisurely stroll, a bit of fishing, or simply to take in the serene beauty of the Maine coast. This attraction is ideal for couples seeking a romantic walk, families looking for an easy outdoor activity, or solo adventurers enjoying the tranquility.

The Maine Narrow Gauge Railroad Company and Museum

Step aboard for a charming journey into Maine’s railroad history at the Maine Narrow Gauge Railroad Company and Museum. What makes this attraction unique is its focus on the narrow-gauge railroads that once crisscrossed the state, crucial for Maine’s logging and industrial heritage.

You can expect a delightful scenic train ride along the Eastern Promenade, offering unique views of Casco Bay and the city from a vintage coach. Before or after your ride, explore the museum, which houses historic locomotives, rolling stock, and exhibits detailing the fascinating story of these smaller, nimble trains. It’s an engaging experience for families with children, history buffs, and train enthusiasts, offering both entertainment and education about a significant part of Maine’s past.

The Shipyard Brewing Company

Portland’s craft beer scene is legendary, and Shipyard Brewing Company is one of its pioneering forces, offering a taste of Maine’s brewing heritage. What makes Shipyard special is its long-standing presence and diverse range of beers, from traditional ales to seasonal favorites like Pumpkinhead.

You can expect to take a self-guided tour of their facility, observing the brewing process through viewing windows, and then head to their tasting room to sample a flight of their popular brews. The atmosphere is casual and lively, making it a great spot to unwind with friends or family after a day of exploring. It’s an ideal stop for beer lovers interested in the origins of Portland’s craft beer boom and anyone looking to enjoy a refreshing local pint.

Plan Your Visit

Portland, Maine, truly is a destination that offers something for every traveler, from the rugged beauty of its lighthouses to the historic charm of its Old Port and the innovative spirit of its culinary and brewing scenes. You’ve now discovered a city where maritime history comes alive, artistic endeavors flourish, and outdoor adventures beckon at every turn. Whether you’re savoring fresh lobster, exploring charming islands, or delving into fascinating museums, Portland promises a rich tapestry of experiences.

Plan your visit during the warmer months to fully enjoy all the outdoor activities, and remember that while Portland can be explored on a budget, splurging on its world-class dining and unique tours is highly recommended. So pack your bags, prepare to be charmed, and immerse yourself in the unforgettable allure of this vibrant New England city. Your Portland adventure awaits!