Portland, Maine: Best Things to Do – Top Picks

Did you know that Portland, Maine has more restaurants per capita than any other U.S. city except San Francisco? This coastal gem packs an impressive culinary punch for its size, with over 300 eateries in a city of just 66,000 residents. But Portland’s appeal extends far beyond its famous lobster rolls and craft breweries. From cobblestone streets lined with 19th-century architecture to stunning coastal views and vibrant cultural attractions, this charming New England city offers a perfect blend of urban sophistication and maritime heritage.

Getting to Portland, Maine

Portland is easily accessible by multiple transportation options, making your journey to this coastal gem straightforward regardless of where you’re coming from.

By Air

The Portland International Jetport (PWM) offers direct flights from major cities including New York, Chicago, Atlanta, and Washington D.C. The airport is conveniently located just 10 minutes from downtown, making for a quick transfer to your accommodations. Looking for the best flight deals? Check out available Flights to start planning your Portland adventure.

By Car

Portland is approximately a 2-hour drive from Boston and 6 hours from New York City. The drive along I-95 offers scenic views, especially as you enter Maine. Once in Portland, you’ll find several parking garages in the downtown area, with rates ranging from $15-30 per day. Consider renting a car to explore beyond the city limits—check out available Rental Cars for your trip.

By Train or Bus

Amtrak’s Downeaster train provides service from Boston to Portland several times daily, with the journey taking about 2.5 hours. Concord Coach Lines and Greyhound also offer bus service to Portland from various Northeast cities.

Best Time to Visit Portland Maine

Portland experiences distinct seasons, each offering a unique perspective on the city’s charm.

Summer (June-August)

The peak tourist season brings warm temperatures (65-80°F) and perfect conditions for exploring the outdoors. Summer festivals abound, including the Old Port Festival and Maine Lobster Festival in nearby Rockland. Expect higher prices and larger crowds, especially on weekends.

Fall (September-October)

Many locals consider fall the perfect time to visit Portland. The stunning foliage transforms the landscape into a canvas of red, orange, and gold. Temperatures remain comfortable (50-65°F), and tourist crowds thin out significantly. This is an ideal time for hiking, photography, and enjoying harvest festivals.

Winter (November-March)

Winter brings a quieter, more intimate Portland experience. While temperatures drop (20-40°F) and snow is common, many restaurants and shops remain open. Winter activities include ice skating at Thompson’s Point and exploring museums. You’ll find the best hotel rates during this season.

Spring (April-May)

As the city awakens from winter, spring offers gradually warming temperatures (45-60°F) and blooming landscapes. This shoulder season provides good value on accommodations before the summer rush, though some coastal attractions may have limited hours.

Where to Stay in Portland

Finding the right neighborhood for your stay can significantly enhance your Portland experience. Each area offers its own unique character and proximity to different attractions.

Top Portland Maine Things to Do

1. Explore the Old Port District

The heart of Portland’s charm lies in its historic Old Port district. Wander through cobblestone streets lined with 19th-century brick buildings housing boutique shops, art galleries, and some of the city’s best restaurants. Exchange Street and Commercial Street offer the highest concentration of shops and eateries. Don’t miss the chance to watch fishing boats unload their daily catch at the working waterfront.

2. Visit Portland Head Light

No trip to Portland is complete without seeing Maine’s oldest lighthouse. Located in nearby Cape Elizabeth at Fort Williams Park, Portland Head Light has stood sentinel since 1791. The dramatic rocky coastline surrounding the lighthouse makes for stunning photographs, especially at sunrise or sunset. The on-site museum details the lighthouse’s fascinating history, and the surrounding park offers picnic areas and walking trails with magnificent ocean views.

3. Sample Local Cuisine

Portland’s food scene has earned national recognition, with an emphasis on farm-to-table dining and fresh seafood. Must-try experiences include:

• Lobster rolls at Portland Lobster Company or Highroller Lobster Co.
• Belgian-style fries at Duckfat, fried in—you guessed it—duck fat
• Potato donuts at The Holy Donut (arrive early before they sell out!)
• Oysters and other fresh seafood at Eventide Oyster Co.
• Craft beer at one of Portland’s 20+ breweries, including Allagash and Shipyard

4. Take a Harbor Cruise

Experience Portland from the water with a scenic cruise of Casco Bay. Options range from historical tours to wildlife watching excursions. Lucky Catch Cruises offers a hands-on lobstering experience where you can help haul traps and learn about sustainable fishing practices. For a more relaxed experience, the Casco Bay Lines ferry service provides transportation to nearby islands and offers sunset cruises with spectacular views of the coastline.

5. Discover the Arts District

Portland’s vibrant arts scene centers around Congress Street. The Portland Museum of Art houses an impressive collection spanning three centuries, including works by Winslow Homer, Claude Monet, and Andy Warhol. First Friday Art Walks (held monthly) transform the district into an open gallery with special exhibitions, street performances, and food vendors. The nearby Maine College of Art adds to the creative energy with student exhibitions throughout the year.

6. Climb the Portland Observatory

Built in 1807, the Portland Observatory is the last remaining maritime signal tower in the United States. Climb the 104 steps to the top for panoramic views of the city, harbor, and surrounding islands. Guided tours provide fascinating insights into Portland’s maritime history and the tower’s role in ship communication before the age of radio.

7. Visit the Victoria Mansion

Step back in time at this opulent Italian villa-style mansion built in the 1860s. Victoria Mansion features extraordinary architectural details, intricate woodwork, and over 90% of its original furnishings. The trompe l’oeil wall paintings create stunning three-dimensional effects that must be seen to be believed. The mansion is particularly magical during the holiday season when it’s decorated in Victorian-era Christmas splendor.

Outdoor Adventures in Portland

Portland’s natural beauty provides the perfect backdrop for outdoor enthusiasts. From coastal trails to island excursions, there’s no shortage of ways to enjoy Maine’s stunning landscapes.

Eastern Promenade Trail

This scenic 2-mile trail follows an old rail line along the eastern edge of the city, offering spectacular views of Casco Bay. Perfect for walking, jogging, or cycling, the trail connects to the East End Beach—Portland’s only public beach. Pack a picnic to enjoy at one of the many benches overlooking the water, or stop at the playground if you’re traveling with children.

Peaks Island

Just a 20-minute ferry ride from Portland, Peaks Island feels worlds away from the city bustle. Rent bicycles to circle the island’s 4-mile perimeter, explore hidden beaches, and enjoy fresh seafood at island restaurants. The World War II Peaks Island Military Reservation offers fascinating bunkers and observation towers to explore. Ferries run regularly from the Casco Bay Lines terminal on Commercial Street.

Kayaking Casco Bay

Experience Portland’s coastline from a unique perspective by kayaking the protected waters of Casco Bay. Several outfitters offer guided tours and equipment rentals for all skill levels. Paddle around the Calendar Islands (named because there are said to be 365 of them), explore hidden coves, and spot wildlife including seals, osprey, and occasionally bald eagles.

Portland Trails Network

The city maintains over 70 miles of trails connecting neighborhoods, parks, and natural areas. The Fore River Sanctuary features Portland’s only natural waterfall, while the Presumpscot River Preserve offers serene forest walks along the riverbank. Maps are available at the visitor center or can be downloaded from the Portland Trails website.

Portland’s Renowned Food Scene

Portland has earned its reputation as one of America’s top food destinations. The city’s culinary landscape blends traditional New England fare with innovative global influences, all built on a foundation of locally-sourced ingredients.

Lobster Experiences

No visit to Portland is complete without sampling Maine’s iconic crustacean. Beyond the classic lobster roll (served either warm with butter or cold with mayo), look for creative interpretations like lobster mac and cheese, lobster tacos, and even lobster ice cream for the adventurous. Top spots include:

• Portland Lobster Company – Waterfront dining with outdoor seating and live music
• Highroller Lobster Co. – Hip spot with creative lobster dishes and house-made brioche rolls
• Luke’s Lobster – Sustainably sourced lobster in a casual setting on Portland Pier

Craft Beer Trail

Portland boasts one of the highest concentrations of craft breweries in the country. Many are clustered in the East Bayside neighborhood, nicknamed “Yeast Bayside” by locals. Popular breweries include:

• Allagash Brewing Company – Known for Belgian-style beers and free tours
• Shipyard Brewing Co. – One of Maine’s original craft breweries
• Bissell Brothers – Trendy spot for hazy IPAs and rotating taps
• Rising Tide Brewing – Family-owned brewery with a spacious tasting room

Consider booking a guided brewery tour if you want to sample multiple locations without worrying about transportation.

Don’t Miss Food Experiences

Day Trips from Portland

While Portland offers plenty to keep you busy, the surrounding region is filled with charming towns and natural wonders worth exploring. Here are some of the best day trips, all within an hour’s drive of the city.

Cape Elizabeth (15 minutes)

Just south of Portland, Cape Elizabeth is home to the iconic Portland Head Light and Fort Williams Park. After visiting the lighthouse, explore the park’s walking trails and ruins of the former military installation. Nearby Two Lights State Park offers dramatic ocean views and rocky shorelines perfect for photography. Don’t miss the lobster rolls at the Lobster Shack at Two Lights or Bite Into Maine’s food truck at Fort Williams Park.

Freeport (20 minutes)

Shopping enthusiasts will love Freeport, home to the flagship L.L.Bean store that’s open 24/7, 365 days a year. Beyond L.L.Bean, you’ll find dozens of outlet stores and local boutiques. Take a break from shopping to visit the Desert of Maine, a curious 40-acre “desert” of glacial silt, or the Wolfe’s Neck Woods State Park for peaceful forest trails along Casco Bay.

Kennebunkport (35 minutes)

This upscale coastal town offers pristine beaches, historic architecture, and a picturesque harbor. Stroll through Dock Square for shopping and dining, visit the First Families Kennebunkport Museum to learn about the Bush family compound, or relax at Goose Rocks Beach. The Clam Shack serves one of Maine’s most acclaimed lobster rolls.

Longer Excursions

Practical Tips for Visiting Portland

Getting Around Portland

Downtown Portland is compact and walkable, especially the Old Port and Arts District. For longer distances or to rest tired feet:

• Metro Bus – The local bus system covers Portland and surrounding communities. Single rides cost $2.00, and day passes are available.
• Rideshare – Uber and Lyft operate throughout the Portland area.
• Bike Rentals – Several shops offer bicycle rentals, perfect for exploring the Eastern Promenade Trail.
• Parking – If driving, use city-operated garages like the Elm Street Garage ($4/hour, $28/day max) for the best rates. Avoid private lots which can charge up to $50/day.

Weather Considerations

Portland’s weather can be unpredictable, even in summer. Pack layers and be prepared for sudden changes:

• Summer temperatures typically range from 65-80°F but can occasionally spike higher
• Evenings cool down significantly, even in summer—bring a light jacket
• Fog can roll in quickly along the coast, especially in the morning
• Winter visitors should pack proper cold-weather gear, including waterproof boots

Money-Saving Tips

Why Portland Should Be Your Next Destination

Portland, Maine offers that rare combination of big-city amenities with small-town charm. From the moment you set foot on its historic cobblestone streets, you’ll understand why this coastal gem continues to captivate visitors year after year. Whether you’re savoring the catch of the day at a waterfront restaurant, exploring the vibrant arts scene, or venturing to nearby natural wonders, Portland delivers experiences that linger in your memory long after you’ve returned home.

The city’s walkable size means you can pack numerous experiences into even a short visit, while its depth of character rewards those who choose to stay longer. And while Portland’s lobster rolls and lighthouses may initially draw you in, it’s the warm local hospitality and authentic maritime culture that will have you planning your return before you’ve even left.