Boats along the pier in Portland, Maine. Photo by iStock

Coastal Maine has long been one of my favorite destinations. Its stunning natural beauty, laid-back vibes, quirky small towns, and rich maritime culture make it unique.

Portland, Maine, with its population of around 68,000, may not be a small town, but it retains a charming, walkable, small-town atmosphere. Nestled on a peninsula in Casco Bay, this city boasts a picturesque setting by the sea.

Luke's Lobster in Portland Maine
Luke’s Lobster in Portland, Maine. Photo by Janna Graber

The West End Historic District has many beautifully renovated Victorian homes. Most are home to local residents, while a few, like the renowned Victoria Mansion, are museums or historical sites.

There would be more historic homes except for the Great Portland Fire of 1866, when two boys playing with fireworks on July 4th caused the largest urban fire in US history at the time.

Portland is a popular destination in Maine, especially in the summer. It can be a bit busy in the high season. I visited in the early fall when the weather was beautiful and the town was not as crowded. Late spring is also an excellent time to visit. 

Maine is well-known for its fall colors. The best time to view the fall colors in Coastal Maine is mid to late October – and that’s an excellent time to visit Portland, too.

Where to Stay in Portland, Maine

The Cambria Portland - Old Port. Photo by Cambria Portland
The Cambria Portland Downtown – Old Port. Photo by Cambria Portland

When planning a trip, the first thing I consider is the accommodation. In Portland, my friend Laurie and I chose to stay at the Cambria Portland Downtown—Old Port. This decision proved to be a wise one as it allowed us to park our car and explore the city on foot, reaching almost all our destinations with ease.

Cambria Portland opened in 2022 in the Old Port neighborhood. It’s just a few minutes’ walk to the Old Port, where you can find restaurants, shopping, and the bustling seaside scene.  

The 102-room Cambria Portland offers a modern luxury experience. The hotel’s décor beautifully reflects the region’s history, creating a unique ambiance.

A room at Cambria Portland Downtown - Old Port. Photo by Cambria Portland
A room at Cambria Portland Downtown – Old Port. Photo by Cambria Portland

We started our mornings with a hearty breakfast at the Alto Terrace Bar + Kitchen and indulged in an exceptional dinner one evening on the spacious patio. The food, prepared with innovative techniques and locally sourced ingredients, was a true culinary delight.  

While we only had a few days to spend in Portland before joining a Maine Windjamming cruise, we made the most of our time.

Here are my recommendations for some top things to do in Portland, Maine.

Explore Portland’s Historic Old Port

The Old Port neighborhood in Portland, Maine. Photo by Amy Sparwasser, iStock
The Old Port neighborhood in Portland, Maine. Photo by Amy Sparwasser, iStock

Portland’s Old Port District is a testament to the city’s rich maritime history and is my favorite part of the city. Its cobbled streets are lined with charming boutiques, art galleries, and cafes housed in centuries-old buildings.

The waterfront scene adds an extra layer of authenticity and charm with sea-worn piers and colorful fishing boats. Laurie and I spent hours exploring the area.

A local artisan in Portland, Maine. Photo by Janna Graber
A local artisan in Portland, Maine. Photo by Janna Graber

We found several small treasures at local shops and bought some jewelry and a Christmas ornament from a local artist.

We sipped drinks on the outdoor patios (Portland has a vibrant craft beer scene) and watched for wayward seagulls who were tempted to steal our snacks.

Sid, the vicious seagull
Seagulls have been known to steal food from unsuspecting visitors. Photo by Janna Graber

See Portland Head Light, Maine’s Oldest Lighthouse.

Portland Head Light is the region’s most iconic symbol. First lit in 1791, the lighthouse played an important role in Maine’s maritime heritage as a beacon of safety for ships navigating the treacherous waters of Casco Bay

The lighthouse still stands on the rugged cliffs of Cape Elizabeth just south of Portland. Its distinctive white tower, made of rubblestone and brick, rises 80 feet above sea level, commanding attention with its classic New England charm.

The light emanating from its lantern room is visible for up to 24 nautical miles. It guides vessels safely into Portland Harbor, marking the entrance to one of the busiest ports on the East Coast.

The Portland Head Light, oldest lighthouse in Maine. Photo by Janna Graber
The Portland Head Light is the oldest lighthouse in Maine. Photo by Janna Graber

While the lighthouse was closed to visitors while we were there, we did tour the adjacent Keepers’ Quarters, built in the early 1800s. The quarters are home to the Museum at Portland Head Light, where exhibits detail the lighthouse’s storied past and the daily lives of its keepers.

The best part of our visit was hiking along the grounds to capture a panoramic view of the Portland Head Light. Crashing waves and rocky shores provided a dramatic backdrop to this historic landmark. The iconic lighthouse is a cherished symbol of Maine’s coastal identity and a must-see when visiting the region.

Laurie and I visited the Portland Head Light on a Portland City and Lighthouse Tour with Portland Discovery Land & Sea Tours. The trolley picked us up in the Old Port area, and we enjoyed the tour guide’s narration as we drove through the city and to the Portland Head Light.

Take a Lobster Boat Tour with Lucky Catch Cruises

Kids enjoy learning about lobster on a tour with Lucky Catch in Portland. Photo by Janna Graber
Kids enjoy learning about lobster on a tour with Lucky Catch in Portland. Photo by Janna Graber

Lobster fishing is an essential industry in Portland, Maine. Families have been lobster fishermen here for generations. We learned more about this unique way of life on a tour with Lucky Catch Cruises in Portland.

Sailing in Casco Bay was half the fun, as we got a wonderful view of Portland Harbor and the city’s skyline. Although we weren’t fishing for lobster on the tour boat, the captain took us to check several of his traps. 

Eager to learn more about this quintessential Maine tradition, we donned colorful aprons and helped pull in a trap. He showed us how to check the size, sex, and weight of the lobsters, and then we returned them to the sea.

The captain then shared his knowledge of sustainable lobstering practices, emphasizing the importance of preserving Maine’s precious marine ecosystem for future generations.

On a walking tour in Portland, Maine.
On a walking tour in Portland, Maine. Photo by Janna Graber

Take a Walking Tour of Portland’s Golden Age

Portland, Maine, is renowned for its rich history, particularly during its “Golden Age” in the 19th century when it flourished as a major seaport and cultural hub. Laurie and I wanted to learn more about this history so we joined a walking tour of Portland’s historic homes.

A volunteer from Greater Portland Landmarks, a non-profit whose mission is to preserve Portland’s historic landmarks, took us on a fascinating tour of the Spring Street/State Street neighborhood, once considered “the most beautiful neighborhood in Portland.

In the 19th century, the city was home to some of its wealthiest and most powerful people, and it still displays some of those classic roots.

Victoria Mansion in Portland, Maine. Photo by Janna Graber
Victoria Mansion in Portland, Maine. Photo by Janna Graber

One fascinating highlight was the Victoria Mansion (Morse-Libby House). Built between 1858 and 1860, Victoria Mansion is a masterpiece of pre-Civil War architecture filled with exquisite furnishings and decorative arts from the period.

We also stopped to see the Wadsworth-Longfellow House, the childhood home of poet Henry Wadsworth Longfellow and his family. Constructed in 1785, the house is one of the oldest standing structures in Portland and is now a museum offering guided tours.

Victorian homes along the Eastern Promenade in Portland, Maine. Photo by Janna Graber
Victorian homes along the Eastern Promenade in Portland, Maine. Photo by Janna Graber

Even if you don’t take the walking tour, stroll along the city’s Eastern Promenade. This scenic waterfront park offers breathtaking views of Casco Bay and features a collection of historic homes along Eastern Promenade Road.

Dining in Portland

Dining is a pleasure in Portland. There’s no shortage of excellent restaurants, many along the sea and with outdoor patios. The dining scene here isn’t flashy or pretentious, and I liked the laid-back vibe. The food was excellent at each place we visited, especially the seafood.

Dining in the Old Port District in Portland, Maine. Photo by Janna Graber
Dining in the Old Port District in Portland, Maine. Photo by Janna Graber

Here are a few of our favorite places to dine in Portland. Reservations are highly recommended if they are available.

  • Scales
    Seaside venue for local seafood, raw bar, wine and New England comfort classics
  • Street & Co
    Upscale dining in a rustic bistro along a cobblestone alley
  • Portland Lobster CO
    Winner of Portland’s Best Lobster Roll several years running
  • The Holy Donut
    These Gourmet Potato Donuts are popular with visitors and locals alike
  • DiMillo’s On the Water
    A seafood restaurant created in a 206-foot ship
  • Luke’s Lobster
    The view from the top floor of this restaurant is amazing
DiMillo’s On the Water
DiMillo’s On the Water is a restaurant on a 206-foot ship. Photo by Janna Graber

How to Get to Portland, Maine

The best way to get to Portland, Maine, largely depends on your starting point and personal preferences. Here are some options:

By Air: Flying into Portland International Jetport (PWM) is often the fastest way to reach Portland if traveling from a distant location. Many major airlines offer direct flights to Portland from various cities. Once you arrive at the airport, you can take a taxi, shuttle, or rental car to reach your final destination in Portland.

By Car: Driving to Portland could be convenient if traveling from nearby states or within New England. Major highways such as I-95, I-295, and US Route 1 connect Portland to other regional cities. Driving gives you flexibility and allows you to explore the surrounding areas at your own pace.

By Train: Amtrak’s Downeaster train service connects Portland to Boston, Massachusetts, with stops along the way. This option offers a scenic ride and can be a relaxing way to travel if you’re coming from Boston or intermediate stations.

By Ferry: If traveling from locations such as Nova Scotia or other parts of Canada, you might consider taking a ferry. The Bay Ferries service operates a seasonal ferry between Bar Harbor, Maine and Yarmouth, Nova Scotia. The ride is approximately 3.5 hours long. You can then drive from Bar Harbor to Portland.

Sunset in Portland, Maine. Photo by Janna Graber
Sunset in Portland, Maine. Photo by Janna Graber

When Is the Best Time to Visit Portland, Maine

The best time to visit Portland depends on your interests and what you hope to experience during your trip.

Summer (June to August): Summer is the peak tourist season in Portland. The weather is generally pleasant with warm temperatures, making it ideal for outdoor activities like exploring the city’s waterfront, visiting nearby beaches, or taking boat tours. However, remember that summer can be crowded, and accommodations may be more expensive.

Fall (September to November): Fall is a popular time to visit Portland, especially for leaf-peeping as the foliage turns vibrant shades of red, orange, and yellow. The weather is still relatively mild in September but cools off towards November. Fall also brings events like harvest festivals and food events featuring Maine’s famous lobster.

Winter (December to February): Winter in Maine has its beauty. The weather can be cold and snowy, but winter might be the time for you if you like quiet winter landscapes or winter sports like skiing or snowboarding. 

Spring (March to May): Spring is a quieter time to visit Portland than summer, with milder temperatures and fewer crowds. It’s a great time to explore the city’s parks, gardens, and hiking trails as nature comes back to life. Spring also brings events like the Portland Flower Show and various food festivals.

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Janna Graber
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