Travel + Discover Portland: Maine Vacation Guide

You don’t visit Portland, Maine, by accident. People who end up here usually have good instincts – for food, for art, for places that aren’t trying so hard to impress you.

Even though Portland is the largest city in Maine, it still rocks small-town vibes with that idyllic Maine energy. It also has grit, an actual skyline, and a lot more going on than just lobster shacks and souvenir shops.

Sure, it has working docks and salty air, but it’s also packed with serious art galleries, studios hidden in old warehouses, indie music spilling out of unexpected corners, and an international collection of restaurants that earn it the title of a foodie town.

While searching for lobsters and lighthouses, you’ll walk in the steps of people like poet Henry Wadsworth Longfellow, author Stephen King, and actress Anna Kendrick.

Plus, there’s about 400 years of history to explore. You might want to extend your trip by a few days.

Where Is Portland, Maine?

Portland is just north of the Southern Maine Coast beaches region, about 50 miles from the state line and 110 miles from Boston. It’s easy to access by car from I-95 or Route 1.

The Amtrak Downeaster offers train ride transportation between Boston and Brunswick, with Portland as the third-to-last stop. Air travelers fly into Portland International Jetport, technically in South Portland, but with easy access to the city, beaches, or craggy coast.

Speaking of South Portland, it’s important to note that it’s a separate city. Beyond that, Cape Elizabeth is home to most of the lighthouses people associate with Portland, including the Portland Head Light.

Portland’s border doesn’t stop at the water. Several islands are within the city limits, too. What does that mean for tourists? Inexpensive ferry rides!

Best Things to Do in Portland

There is much to see and do, depending on how much time you plan to spend in Portland. Between Maine shopping, exploring the Old Port, gourmet dining, historic tours, and boat rides, there is truly something for everyone to enjoy!

Experience the Old Port District

The Old Port district is known for its chic boutique shopping, renowned dining, and bustling nightlife. The shopping includes exquisite crafts from local artists and designers.

The revitalized warehouse district – with cobblestone streets, old brick buildings, and quaint fishing piers – makes you think of ditching your life and turning to lobstering.

Old banks and warehouse buildings have been transformed into shops, apartments, restaurants, and office spaces with original and unique architectural features.

Take a walk along Commercial Street and experience one of the few working waterfronts left in the United States. At night and on weekends, the Old Port comes alive with entertainment and nightlife at the many bars, brewpubs, and event spaces in the area.

Wander Through the Portland Museum of Art

The Portland Museum of Art is a fascinating place to visit. It’s the most prominent and oldest art institution in Maine and was designed by renowned architect I.M. Pei.

This avant-garde museum is all about creative expression that’s one-of-a-kind, so you’re likely to find art in media and concepts that you’ve never seen before. The exhibits here change regularly but feature everyone from classical artists to contemporary, local painters and sculptors.

Also, you’ll see some truly famous artists’ work displayed here, including Andy Warhol, Mary Cassatt, Edgar Degas, and Claude Monet.

Burn Energy at the Children’s Museum + Theatre of Maine

Next door to the Portland Museum of Art is the Children’s Museum + Theatre of Maine, oriented for kids of all ages. The museum features vast diversions for kids, including a small park for toddlers, a cave and farm area, interactive science exhibits, a space shuttle, and Maddy’s Theatre.

Peruse More of the Arts District

Portland is known as a cultural hot spot for artists. The Arts District is located on much of Congress Street, toward the West End.

Here, you’ll find many art galleries, museums, theaters, and even the Maine College of Art & Design. The First Friday Art Walk occurs on the first Friday of every month. Local galleries and museums are open to the public with free food and drink.

Maine Historical Society and the Wadsworth-Longfellow House

No trip to Portland, Maine, is complete without visiting the historical museum and the  Wadsworth-Longfellow House, where Henry Wadsworth Longfellow lived.

Whether you visit one or both of the treasured museums, you can guide yourself through history or wait for a docent-led tour. Walking tours are also offered seasonally.

Climb The Portland Observatory

Nautical buffs will enjoy a visit to The Portland Observatory on Munjoy Hill. Built in 1807, the observatory is the last wooden signal tower in North America. It’s also one of the few structures that survived the Great Fire of 1866.

The observatory offers great views of Portland, Casco Bay, Back Cove, and Mt. Washington. It’s owned and operated by the City of Portland and Greater Portland Landmarks, which offer guided tours during the summer season.

Ride a Train at the Maine Narrow Gauge Railroad Co. & Museum

Train enthusiasts and history lovers will want to pay a visit to the Maine Narrow Gauge Railroad Co. & Museum. This museum pays homage to the history of the narrow gauge railroad system that played a vital role in Maine’s development in the 19th century.

These unique, extra-small trains and tracks made it possible to wind throughout Maine’s hilly terrain. You’re welcome to learn at the museum, view the exhibits, and even ride on a working historical train!

During the holidays, you can find a working Polar Express train featuring Santa and Christmas music.

Explore The Eastern Promenade

Arguably, this is the most scenic point in the city of Portland, with the island masses spread across the Casco Bay waters in view. The Eastern Prom, as its abbreviated reference, features a small park for the kids, a trail system with historic references, and the Maine Narrow Gauge Railroad. Concerts and fireworks for the 4th of July are centered here, too.

East End Beach is the central gathering spot for sunrises and sunny days. The Eastern Promenade Trail hugs the coastline for two miles of views and history. Great people watching, too! 

Keep walking the trail to get to Fort Allen Park, a historical site dating back to the 1700s and still a popular place for live music at the bandstand. 

Discover the Portland Trails Network

Beyond the Eastern Prom, Portland Trails creates and maintains a network of trails extending about 80 miles. Preservation of green space is always a goal tied to Maine roots.

There are more than 40 trails in the Greater Portland & Casco Bay region, some of which include forests, waterfalls, water views, and wetlands. Plus, trails are four-season activity hubs with many offering cross-country skiing, snowshoeing, or sledding.

Visit Fort Gorges

It might seem weird to suggest visiting a fort that never saw a battle or even had troops stationed there, but Fort Gorges is impressive nonetheless. It’s just offshore from Portland, and the entire island is the fort – almost like it rises from the depths of the bay.

Sail With Fogg’s Water Taxi

If you stop when you see the name Fogg’s Water Taxi, you’ll miss one of the best boating experiences in Portland, Maine. Charter your ride and set your course, or choose one of the standard cruises that include happy hour, sunset rides, and food cruises to nearby lighthouses.

Hit the Disco Scene at Bubba’s Sulky Lounge

Portland is known for its food, history, and natural beauty, but that doesn’t mean there’s no nightlife. Bubba’s Sulky Lounge is the place to be on weekends.

This retro-style club brings you back to the dance scene of the late 60s and 70s with a light-up rainbow dance floor and colorful lights all around.

This is the place to go over the top, and you’ll find plenty of costume parties and fun events going on all year. Bubba’s has two dance floors and plenty to eat and drink, so come prepared for a good time!

Discover More Nightlife Spots

At night, Portland is bustling with locals and visitors who have come to enjoy the city’s nightlife.

It’s full of sports bars, cocktail lounges, and nightclubs, offering something different for everyone – whether you choose to sip a beer and enjoy the game, chat with old friends over cocktails in a wine bar, or dance to some of the hottest local DJs.

Watch a Performance at the Cross Insurance Arena

The Cross Insurance Arena in Portland’s Old Port is the hub of trendy events coming and going through Portland.

Here, you can see all kinds of hip and relevant music performers and shows – the Black Keys, American Idol, Cirque du Soleil, the Maine Mariners, the Portland Pirates, and Disney on Ice.

Watch the Portland Sea Dogs Play

For sports enthusiasts, a Portland Sea Dogs baseball game is fun for the whole family. As the Minor League affiliate of the Boston Red Sox, Sea Dogs games draw fans of all ages to cheer on future big leaguers and watch some impressive baseball.

From late April to early September, tickets are incredibly affordable. There’s always something fun going on at Hadlock Field – from contests and giveaways to games and entertainment from Slugger the Sea Dog, the team’s mascot.

Go on a Food Tour

In recent years, Portland has become a destination for foodies. Though the town is famous for its seafood, you can find cuisines of all kinds in this coastal paradise!

Maine Day Ventures offers culinary tours of the city, giving you the chance to hit up all the most unique and amazing eateries in Portland. It’s ideal if you’re only in town for a short time but would still like to experience all the culinary delights.

You can also choose to do a themed tour, hitting all the seafood restaurants on the Old Port Seafood Lovers Tour or the best watering holes on the It’s Happy Hour Time tour.

For beer lovers, Portland has the highest concentration of microbreweries in the country, with many offering tours and tastings. Maine Brews Cruise tours take you around to the Portland breweries. It’s a fun way to let someone else drive while you drink the local craft brews.

Go on a Lobster Cruise

If there’s one thing that coastal Maine is known for, it’s lobster! If you’ve ever been curious about how Maine lobsters are caught and prepared, you might enjoy a lobster cruise.

Lucky Catch Cruises offers tours that last for roughly 90 minutes. These give you the chance to hit the ocean with professional lobster fishermen to see how they trap the state’s most famous seafood delicacy. You can even participate in hauling in the traps.

Do you prefer to sit back and observe? The scenery is unmissable, including the coastal seal rocks and historic lighthouses.

Relax at Deering Oaks Park

For peace and green spaces in Portland, go to Deering Oaks Park, a short drive from the Old Port. It features a small pond at its center with a splendid water fountain, which looks lovely in the rising and falling sun.

In fall, Camp Sunshine lights up the park with thousands of Jack-o’-lanterns. In the winter months, the frozen pond is open for free public ice skating.

This scene might look familiar; it’s where Denzel Washington and Whitney Houston shot a scene from the movie “The Preacher’s Wife” in the mid-1990s.

Visit Peaks Island & Other Islands

Many of Casco Bay’s islands bring you into a seemingly different world in stark contrast to the culture, city hotels, and cobblestone streets you left behind in the city.

Many of them serve as summer destinations and day trip excursions for scenic bike rides, nature walks, or beach visits.

Peaks Island is located just off the coast, a few miles from Portland. This small island is a popular spot for outdoor sports enthusiasts of all kinds. One of those trails we told you about loops for 2 miles around this island.

The untamed island can be explored via hiking, kayaking, or cycling, and there are many state parks and beaches. Alternatively, tour some of the historic lighthouses or military bunkers.

If history or hiking isn’t your thing, don’t worry. The island is also home to some fantastic restaurants and shopping, so there’s something for everyone to enjoy.

Also, Stream Reggae at Jones Landing is a very popular afternoon of music, dancing, and drinks.

Getting to the Casco Bay Islands

You’ll have to take a ferry across the bay to get there. Casco Bay Lines, located in Portland Harbor, can take you to beautiful nearby islands for day trips or sunset cruises.

The ferries run year-round and travel to Peaks Island, Little Diamond Island, Great Diamond Island, Diamond Cove, Long Island, Chebeague Island, Cliff Island, and Bailey Island.

Portland, Maine, Events to Attend

First Friday Art Walk

Every first Friday of the month, the sidewalks along the Art District and Old Port turn into a bazaar of locally crafted items, Maine art, and live musical and dance performances. Art galleries and studios open their doors for free exhibitions, as well as wine tastings and snacks.

The First Friday after Christmas marks the most marvelous First Friday event as trees and buildings are adorned with lights. Parts of the Art District, including Congress St, are blocked off for pedestrians to walk freely through the streets of Portland.

Victoria Mansion at Christmas

During the holidays, Victoria Mansion is decorated in classic holiday splendor with tours of this gracious historic 1858 pre-Civil War home. You can tour Victoria Mansion year-round, or rent it for posh private parties on Danforth Street in Portland.

Portland Maine Comedy Festival

The Portland Maine Comedy Festival brings stand-up comedians from across the country into the city’s bars, breweries, and small theaters every summer.

It’s low-key but packed with talent, blending local acts with nationally touring comics. Don’t be surprised if your favorite Instagram or TikTok comedian is here.

Harvest on the Harbor

Harvest on the Harbor is Portland’s way of showing off what it does best: food, drinks, and a serious commitment to flavor. The multi-day event pulls in top chefs, distillers, brewers, and makers for tastings, dinners, and hands-on events.

It’s less of a food festival and more of a flex – proving that Maine’s culinary scene runs a lot deeper than just lobster rolls and chowder.

Portland Chamber Music Festival

The Portland Chamber Music Festival makes classical music feel personal, not buttoned-up. Every August, it brings world-class musicians into smaller venues around the city, mixing traditional chamber pieces with new and unexpected works.

It’s the kind of festival where you might end up 5 feet from the stage, hearing a violin in a way you didn’t know was possible – no fancy dress code required.

Maine Open Lighthouse Day

With so many lighthouses nearby, it makes sense to plan a trip to Portland around Maine Open Lighthouse Day. Since many towers aren’t open to tourists, this is the one day of the year when places like the Portland Head Light let people in.

This annual event happens on the second Saturday in September.

Where to Eat in Portland

Even if you only have one day in Portland, dining at a world-renowned restaurant is a must. Portland was voted America’s Foodiest Small Town by Bon Appétit in 2009 for its variety, each serving unique and delicious plates for your tasting pleasure.

Portland restaurants have everything from fresh seafood, raw oyster bars, and mouthwatering lobster to Italian, Irish, Asian, and Mexican cuisine. Dine by the water at several choice restaurants, including DiMillo’s floating restaurant.

Or, go to one of the smaller, charming Old Port settings with exposed brick walls, high ceilings, and windows. There are more modern eateries to check out, too.

Leeward

This upscale Italian-inspired eatery features deliciously fresh pasta dishes, local morels and squash blossoms, seafood, and other delicate bites that are sure to leave you intrigued but satisfied.

Even Conde Nast wrote that, “Leeward is the embodiment of just the kind of mom-and-pop-gone-perfectionist restaurant that Portland excels at.”

Crispy Gài

Crispy Gài is a Thai-inspired casual eatery in Portland, Maine. The menu features delicious dinner and brunch items influenced by the cuisine of Bangkok.

You’ll find fried chicken, curry, fried oyster mushrooms, and other delectable eats here, as well as signature cocktails fusing American cocktail culture with classic Thai flavors like pineapple, coconut, and lemongrass.

Terlingua

The intersection of Texas barbecue and Mexican fusion comes together at Terlingua.  This combination deli, butcher, and barbecue restaurant offers all kinds of fresh meat dishes sourced from local farmers.

If you want to stop in for a full meal, you’ll find shared plates, as well as freshly made brisket, carnitas, chili, and more. Alternatively, you can simply order the freshest cuts of the day for eating in the store or at home!

Scales

Everyone knows that Portland is the place to get some of the best seafood you can find anywhere in the United States. Scales is one of the best, and it’s definitely worth a visit if you’re looking for some delicious fish, lobster, oysters, mussels, or other delicacies.

The menu here rotates seasonally to ensure that you’re served only the freshest, most scrumptious seafood and produce.

Also, Scales has a raw bar where you’ll find freshly caught oysters and clams on the half shell, as well as kingfish and tuna crudo, tuna tartare, and halibut ceviche. Valet parking is free, on top of all that!

Izakaya Minato

Izakaya Minato is the place in Portland to find high-end Japanese cuisine. This elegant restaurant combines the tradition of izakaya cooking with fresh, seasonal Maine ingredients.

You’ll find menu classics – such as Japanese grilled chicken, grilled fish, and sashimi. If you aren’t familiar with Japanese fare, you can ask for the chef’s choice.

In addition to these delicious menu options, you’ll find a full bar with a wide selection of craft beer, sake, and Japanese whiskey options. All this makes it possible to enjoy the unique fusion of Japan and coastal Maine!

Rigby Yard

Rigby Yard pulls double duty in Portland’s Old Port – part coffee shop, part bar, and all-around solid hangout. During the day, it’s a laid-back spot to grab a Time & Tide coffee, catch up on work, or just loiter with free Wi-Fi.

At night, it flips into a lively space with Maine craft beer, smart cocktails, and comfort food that’s a few steps above basic. Industrial but warm, its decor nods to the railroad history of Portland.

Twelve

Twelve isn’t just another Portland restaurant riding the local-food wave. It’s the real deal. Set inside a rebuilt 127-year-old train foundry, it pairs history with a modern, stripped-down style that actually feels cool, not forced.

The team has serious cred (think Eleven Madison Park and Cafe Boulud), and the menu leans hard into Maine-sourced ingredients with a four-course setup that changes with the seasons. If you want a flex meal without the pretense, this is it.

Central Provisions

It’s easy to overeat in Portland and be full through the next meal. That’s why we love Central Provisions and its small-plate menu.

Try the raft cocktails or Maine-made beers and wines. The restaurant is housed in a building dating back to Portland’s early shipping days. It’s a local favorite spot.

About Portland & Its History

Portland, Maine, is the largest city in the state but has the charm of a classic seacoast town. This coastal area is a popular summer spot for tourists all over the Eastern Seaboard because it has access to beaches, forests, and many other landscapes in the Southern Maine Coast.

While the city is a congregation of a historic waterfront, art communities, hole-in-the-wall pubs, top-chef restaurants, sidewalk performances, antique and art shops, and nightclubs, it’s still small enough that you’ll have the streets memorized by the time you leave.

Developing New England

Founded in 1623, Portland predates the American Revolution by more than 150 years and was instrumental in the development of New England at the time. It also played an important role in isolated battles of the French and Indian Wars, the American Revolution, and the War of 1812.

In addition, Portland was an important shipping port between Canada and the United States, as well as Europe. The Port of Portland remains essential to the city’s economy. As the second-largest port in New England, it’s a vital part of the commercial fishing and shipping industries.

Devastating Fires & Economic Crisis

Throughout its history, Portland has endured four devastating fires. The most famous of these was the Great Portland Fire of 1866.

That fire destroyed a vast portion of the city and robbed 10,000 people of their homes. After this, the city adopted an official emblem depicting a phoenix rising from the ashes.

Throughout the latter half of the 20th century, Portland was in economic crisis, and its infrastructure was crumbling.

During the 1990s, the city became the center of a revitalization effort that focused on updating old buildings for modern use. This included adding more hotels, restaurants, museums, retail outlets, and houses.

Modern-Day Portland

Today, Portland is a popular tourist attraction known for its excellent restaurants, historic buildings, art galleries, and access to Southern Maine beaches and state parks.

In recent years, it has gained a reputation as having a “hipster” scene thanks to an emphasis on contemporary art and modern, locally-sourced restaurants.

The city has transformed its former seaport into a hub of retail and dining in a neighborhood now known as the Old Port. This is a popular spot for locals and Maine tourists to walk and sightsee, mainly since it features some of Portland’s oldest existing buildings.

Portland, Maine: Easy to Love, Hard to Leave

Whether you’re here for a weekend or a full getaway, Portland has a way of pulling you in. It’s the kind of place where cobblestone streets lead to cozy cafés, and every turn offers something new to discover.

With its perfect blend of salty air, creative energy, and small-town feel, Portland makes relaxing feel effortless. Once you visit, it’s easy to see why so many people come back again and again. Fortunately, there are lodging options for every preference, too.