How to Spend the Perfect Weekend in Portland, Maine

The Perfect Weekend in Portland, Maine

Portland, Maine has wiggled its way to the top of our list of favorite cities in America. In fact, I debated even writing a blogpost about it because I’m scared the secret will get out! But, when we find a great place that encourages tourism, we want to share it with you.

This city has to much to offer: great coffee, local breweries, delicious food, beautiful parks, history, and more. However, what really makes this place stand out to us is the people. Some of the nicest people we’ve met across America are the people in Maine. Not gonna lie, it sort of surprised us because New Englanders don’t have the most hospitable reputation across most of the USA. But alas, it’s true. These people are incredibly welcoming and smile at you when you pass on the sidewalk. When you order a cup of coffee they ask about your weekend and genuinely want to know what fun adventures you had on your days off.

But don’t take our word for it, visit Portland, Maine and see for yourself! To get you started we’ve compiled a list of must see places in the city. Do keep in mind that while Portland is the biggest city in the state of Maine, it’s a hop, skip, and a jump away from loads of other adventures including Acadia National Park and picture perfect coastal towns like Camden, Maine. If you have more than just a couple of days in Maine, we'd encourage you to day trip out of the city to some these other noteworthy places.

Without further ado, here is our guide and itinerary to the perfect weekend in Portland, Maine.

Looking for something specific? Jump to a section using the links below.

General F.A.Q.

Before we set sail to the Pine Tree State, here are some essential FAQs that will help you prepare for your trip.

Q: Where is Portland, Maine?

A: Portland, Maine is a picturesque coastal city located in the southeastern part of the state, known for its vibrant cultural scene and historic maritime atmosphere. Maine is the northeastern most state in the lower 48 states of the U.S.A.

Q: What's the weather like in Portland, Maine?

A: Portland experiences four distinct seasons. Winters are cold and snowy, while summers are mild and pleasant, perfect for outdoor activities. Fall is renowned for its stunning foliage, and spring is just starting to bloom.

Q: Do I need a car to get around Portland, Maine?

A: While a car makes it easier to explore the surrounding areas, Portland itself is walkable and has a convenient public transportation system.

Q: What is the currency used in Portland, Maine?

A: Portland, Maine, is part of the United States, so the currency used is the U.S. dollar.

Q: Is the city pet-friendly?

A: Absolutely! Portland is known for its pet-friendly establishments and outdoor spaces, so feel free to bring your furry friend along for the adventure.

Q: Is Portland, Maine safe?

A: Yes, Portland is considered one of the safest cities in the U.S., with a low crime rate and warm, welcoming locals.

Now that we’re acquainted with Portland, Maine, it’s time to chart our course for a weekend you won’t soon forget.

When to visit Portland, Maine

Timing is everything, and the best time to visit Portland largely depends on your interests. Here's a snippet to help you choose:

High Season (June to August): The warm summer months are bustling with tourists, offering the most activities, festivals, and events.

Shoulder Season (April to May, and September to October): Enjoy mild weather, fewer crowds, and the stunning colors of fall.

Low Season (November to March): Winter sports enthusiasts can enjoy skiing and snowboarding in the surrounding areas, while the city lights up with holiday cheer.

Visiting during the shoulder season has the added benefit of lower accommodation rates, making it perfect for those looking to escape the crowds without sacrificing the charm of Portland’s local scene.

Infographic of Portland, Maine average temperatures and rainfall provided by NOAA.

How to get there

Getting to Portland, Maine, is a breeze whether you're flying or driving. The city is served by Portland International Jetport (PWM), despite its name, it primarily offers domestic flights. It's conveniently located just a few miles from downtown, making the transfer to the city quick and easy. Portland International Jetport (PWM) hosts flights from several major airlines including Delta, Southwest, American Airlines, United, JetBlue, and Frontier.

If you're hitting the road, Portland is accessible via several major interstates. Interstate 95 (I-95) runs north to south, connecting the city to the rest of Maine and the northeastern United States, while Interstate 295 (I-295) serves as a shortcut through downtown Portland, allowing for easier access to many of the city’s attractions. Whether you're coming from afar or driving in from a nearby state, Portland's excellent connectivity makes it an appealing destination for travelers.

Boston, Massachusetts to Portland, Maine: 112 mi | 1 hr 45 min | Google Maps

Hartford, Connecticut to Portland, Maine: 200 mi | 3 hr 1 min | Google Maps

New York City, New York to Portland, Maine: 314 mi | 5 hr 28 min | Google Maps

Given this region's dense population, it's no surprise that the roads can become congested, particularly during peak travel seasons and hours. This can significantly extend drive times. For those coming from other areas in the Northeast, trains offer a fantastic alternative, providing a stress-free and scenic route into Portland, Maine, where you can relax and enjoy the journey without the worry of traffic.

Where to stay in Portland, Maine

Portland boasts a variety of accommodation options to suit all tastes and budgets. From historic inns to modern boutique hotels, there’s something for everyone.

Best hotels in Portland, Maine

The Press Hotel

Built within the historic building that once housed Portland's largest newspaper, The Press Hotel exudes charm and sophistication. Guests can enjoy the hotel's attention to detail and nods to its journalistic past, particularly in the typewriter-themed decor. It's centrally located, offering easy access to Portland's best dining, shopping, and cultural attractions.

Note: This is a Marriott property and is a part of their Autograph Collection.

Address: 119 Exchange St, Portland, ME 04101 | Google Maps


Portland Harbor Hotel

Nestled in the heart of the Old Port, the Portland Harbor Hotel stands as a beacon of luxury. Its rooms offer stunning views of Portland Harbor, alongside amenities that cater to every whim. The hotel's restaurant, renowned for its exquisite local cuisine, makes for an unforgettable dining experience.

Address: 468 Fore St, Portland, ME 04101 | Google Maps


The Westin Portland Harborview

Offering panoramic views of Portland and Casco Bay, The Westin Portland Harborview combines modern luxury with unmatched location. Its historic charm, dating back to its opening in 1927, is complemented by contemporary amenities, including the iconic rooftop lounge. Guests can also indulge in the hotel's spa services, designed to rejuvenate and refresh.

Address: 157 High St, Portland, ME 04101 | Google Maps


Canopy by Hilton Portland Waterfront

The Canopy by Hilton Portland Waterfront is the epitome of modern luxury, with a vibrant design reflecting the maritime spirit of Portland. Guests can relish in the hotel's waterfront location, which makes for easy access to boat tours and seafood markets. The hotel also prides itself on offering locally sourced food and drinks, allowing guests to taste the best of Maine.

Address: 9 Center St, Portland, ME 04101 | Google Maps


Bed and breakfast options

Blind Tiger Portland

Housed in a beautifully restored 19th-century mansion, Blind Tiger Portland offers a unique blend of historical elegance and modern comforts. Guests are treated to meticulously decorated rooms that evoke the charm of a bygone era, while still providing all the contemporary amenities necessary for a comfortable stay. The inn is renowned for its warm hospitality and delicious breakfast, making it an ideal choice for travelers seeking a personalized, intimate experience in the heart of Portland.

Address: 46 Carleton St, Portland, ME 04102 | Google Maps


The Chadwick Bed & Breakfast

The Chadwick Bed & Breakfast stands as a testament to timeless elegance and personalized service. Nestled in Portland's picturesque West End, this charming retreat combines modern luxury with quintessential New England hospitality. Each room is uniquely decorated, ensuring a cozy and distinctive stay, while gourmet breakfasts cater to all tastes with locally sourced ingredients. Perfect for those seeking a serene getaway, The Chadwick offers a peaceful haven amidst the vibrant cultural tapestry of Portland.

Address: 140 Chadwick St, Portland, ME 04102 | Google Maps


Pomegranate Inn

Nestled in the heart of Portland's historic West End, the Pomegranate Inn is a delightful escape that offers a unique blend of artsy charm and casual elegance. Each room is individually decorated with vibrant, eclectic art and furnishings, providing guests with an immersive and visually stimulating experience. Known for its warm hospitality and delicious breakfasts, the Pomegranate Inn promises a memorable stay that captures the creative spirit of Portland.

Address: 49 Neal St, Portland, ME 04102 | Google Maps


Portland Head Light at sunrise, Portland Maine
Sunrise at Portland Head Light, Portland, Maine

What to do in Portland, Maine

With two days to play, there’s a wealth of activities and attractions to fill your Portland itinerary. Here are some highlights that are not to be missed.

Embark on a harbor cruise

Exploring Portland from the water offers a unique perspective of the city's maritime heritage and scenic waterfronts. A harbor cruise allows you to soak in the panoramic views of lighthouses, islands, and the bustling harbor life. Whether you opt for a narrated sightseeing tour, a serene sunset cruise, or even a lobster haul experience, you'll find yourself immersed in the rich history and natural beauty that define Portland Harbor.

Visit the Portland Head Light

Situated on the stunning shores of Fort Williams Park, the Portland Head Light stands as one of Maine's most beloved landmarks. Its historic significance and picturesque setting make it a must-visit for anyone touring the Portland area. The lighthouse, commissioned by George Washington himself and first lit in 1791, offers a peek into the maritime history that has shaped much of New England’s coast. Visitors can enjoy breathtaking views of the rugged coastline and sprawling ocean, as well as explore the adjacent museum housed within the former keeper's quarters, providing a deeper insight into the lighthouse's operational past and cultural impact.

Address: Cape Elizabeth, ME 04107 | Google Maps

Take a scenic drive up Highway 1

Driving up Highway 1 presents an unforgettable experience, revealing the rugged beauty and charming small towns of Maine's coastline. This scenic drive offers panoramic views of the Atlantic Ocean, access to quaint shops and local eateries, and the chance to discover hidden gems along the way. Whether seeking a leisurely drive to soak in the scenic vistas or an adventure-filled day exploring coastal attractions, Highway 1 provides a picturesque route that captivates travelers with its natural beauty and cultural richness.

Camden, Maine
Camden, Maine is one of the best small towns in Maine and it's located right on Highway 1.

Enjoy a picnic at the Promenade

Ending a day of exploration on a relaxing note, the Eastern Promenade offers an ideal setting for a leisurely picnic with stunning views of Casco Bay. This spacious, grassy area is perfect for spreading out a blanket and enjoying a meal amidst a backdrop of passing boats and the distant lighthouse. With its peaceful atmosphere and scenic surroundings, the Promenade provides a picturesque escape from the hustle and bustle, allowing visitors to unwind and reflect on the day's adventures.

Address: 49 Eastern Promenade, Portland, ME 04101 | Google Maps

Visit a museum or gallery

Portland, Maine, not only charms its visitors with scenic beauty and maritime adventures but also offers a rich tapestry of cultural experiences through its museums and galleries. Among the most popular is the Portland Museum of Art, which houses an impressive collection of artworks ranging from 18th-century European pieces to contemporary American art. Another notable mention is the Maine Historical Society Museum, offering insights into Maine's fascinating history and cultural heritage through its exhibitions and collections. For a more hands-on experience, the Children's Museum & Theatre of Maine provides interactive exhibits that engage young minds in the marvels of science, culture, and arts.

Take a ferry to experience Maine's idea of "island life"

For a truly immersive experience of Maine's coastal charm, taking a ferry to one of the many surrounding islands is a must. Each island offers its own unique slice of serene beauty and rustic living, allowing visitors to step into a world away from the hustle and bustle of city life. Whether it's for a few hours or a full day, exploring the islands provides a glimpse into the laid-back, closely-knit communities and breathtaking natural landscapes that define Maine's "island life." Among the most popular islands to visit near Portland, Maine, are Peaks Island, Great Diamond Island, and Chebeague Island, each offering unique attractions and serene landscapes.

Visit the L.L. Bean store

No visit to Maine is complete without a trip to the iconic L.L. Bean store in Freeport, just a short drive from Portland. Known for its high-quality outdoor wear and equipment, this flagship store is a destination in itself, operating 24 hours a day, 365 days a year. Beyond shopping, the L.L. Bean campus hosts a variety of outdoor adventures and workshops, from kayaking and archery to bird watching and snowshoeing, making it a must-visit for outdoor enthusiasts and casual visitors alike. Whether you're looking to gear up for your next adventure or simply explore the vast array of products and activities, the L.L. Bean store offers an experience that embodies the spirit of Maine's outdoors.

Address: 1 Freeport Village Station, Freeport, ME 04033 | Google Maps

Sip your way through a craft brewery tour

Portland, Maine, has established itself as a haven for craft beer enthusiasts, boasting an impressive array of breweries that capture the essence of the state's rich brewing tradition. Among the most celebrated spots is Allagash Brewing Company, known for its Belgian-inspired beers and commitment to quality. Equally noteworthy is Foundation Brewing Company, which offers a diverse selection of innovative ales that push the boundaries of traditional flavors. Another must-visit is Rising Tide Brewing Company, where the focus on small-batch, handcrafted beers complements Portland's vibrant food and arts scene. These breweries, along with the city's many other establishments, provide a comprehensive taste of Portland's dynamic craft beer culture.

Portland, Maine brewery pouring beer into a glass from the tap
Brewery scene in Portland, Maine is impressive for a relatively small city!

Take a morning stroll on the Back-Cove Trail

Taking a morning stroll on the Back-Cove Trail is a wonderful way to start the day in Portland. This well-maintained walking and biking path loops around a picturesque tidal basin offering sweeping views of the city skyline against the backdrop of nature's tranquility. It's a favorite among locals and visitors alike for its accessibility and the peaceful escape it provides from urban life. The trail, stretching approximately 3.5 miles, is also a great spot for bird watching, jogging, or simply enjoying a leisurely walk amidst the scenic beauty of Portland.

Address: Portland, ME 04101, United States | Google Maps

Shop and stroll in the Old Port

The Old Port district, with its cobblestone streets and waterfront setting, encapsulates the essence of Portland's rich history and contemporary vibrancy. This bustling area is home to an eclectic mix of shops, galleries, and restaurants, where visitors can find everything from handcrafted Maine goods to the latest fashion trends. Strolling through the Old Port, one is enveloped in the charming atmosphere of this historic fishing port turned modern cultural hub, offering numerous opportunities for dining, shopping, and simply soaking up the local flavor amidst the backdrop of picturesque harbor views.

Address: Google Maps

Old Port, Portland, Maine
Old Port, Portland, Maine

Self-guided walking tour of the city

Exploring Portland on foot with a self-guided walking tour is an excellent way to immerse oneself in the city's rich history and vibrant culture. Visitors can meander through the charming Old Port district, where cobblestone streets and historic buildings tell the tale of Portland's maritime past. Along the way, be sure to visit the landmark Portland Observatory, offering panoramic views of the city and harbor. Each step reveals a new facet of Portland's diverse heritage, from its well-preserved architecture to the bustling arts scene, making it a must-do activity for anyone wanting to truly experience the essence of the city.

Shop at the Portland Farmers' Market

The Portland Farmers' Market is a vibrant gathering place for locals and visitors seeking the freshest produce, artisanal foods, and handmade goods. Open from early spring through late fall, it offers a bounty of seasonal delights that reflect Maine's rich agricultural heritage. Saturdays come alive as vendors from across the region showcase everything from organic vegetables and hand-crafted cheeses to locally sourced meats and artisan breads, making it an essential stop for anyone looking to experience the local flavor of Portland.

Address: 92 Deering Ave, Portland, ME 04102, United State | Google Maps

Bag of potato donuts from the Holy Donut, Portland, Maine
Iced lattes outside at Tandem Coffee, Portland, Maine

What to eat and drink in Portland, Maine

Portland, Maine is a culinary gem that prides itself on offering a wide array of dining options, from cozy cafes to upscale eateries. The city's proximity to the ocean means seafood lovers are in for a treat, with fresh catches featured prominently on many menus. Maine is most famous for its lobster, and Portland's restaurants serve it up in a myriad of ways, from the traditional lobster roll, bursting with succulent meat, to inventive dishes that fuse local flavors with international cuisine. Beyond seafood, the city's food scene is remarkably diverse, featuring everything from hearty New England fare to globally-inspired dishes. Whether you're craving a casual meal or a fine dining experience, Portland's culinary landscape promises an adventure for your taste buds, with the iconic Maine lobster as a must-try highlight.

Be sure to checkout our entire travel guide to the best places to eat and drink in Portland, Maine for our full list of recommendations.

Eastern Promenade, Portland, Maine

Weekend Itinerary

Feeling inspired? Then here's an itinerary that weaves together the essence of Portland into a perfect weekend getaway.

Day 1

  • Morning: Start your day with coffee and a donut at Holy Donut. Famous for their unique potato-based donuts, this is a can't miss spot in Portland, Maine.
  • Late Morning: Spend the afternoon exploring Portland’s local flavor. Visit the arts district, pick up fresh produce at the Portland Farmer’s Market, or sip on coffee at Tandem Coffee Roasters. Note: The Farmers' Market is only open on Saturdays from 7:00 AM - 1:00 PM.
  • Lunch: Grab a casual lunch at The Honey Paw which is famous for its blended cuisine featuring Asian and Maine flavors in a contemporary bistro setting.
  • Afternoon: Explore the city's waterfront and historic docks and stop into some of the shops in the Old Port district.
  • Evening: Savor dinner at Eventide Oyster Co. which offers a modern taken on an traditional oyster bar. If you're not a fan of oysters, consider visiting Fore Street Restaurant which is best known for it's wood-fire grill and over with give a smoky flavor to their upscale American cuisine.

Day 2

  • Morning: Start by grabbing coffee at Bard Coffee before driving out to Fort Williams Park to see the Portland Head Light.
  • Late Morning: Set sail on a harbor cruise with Casco Bay Lines. Admire the coastal scenery and learn about the city’s rich maritime history.
  • Lunch: Have a casual lunch at Duck Fat where you can indulge in Belgian fries cooked in duck fat or their original sandwiches or craft sodas.
  • Afternoon: Wander through the city on foot or by bike. Discover hidden alleys, public art, and local charm. Take a self-guided walking tour of the many historic buildings and landmarks. Or if you prefer to get out of the city for a bit, consider driving scenic Highway 1 up the coast of Maine. You could take as little or as long as you'd like to do this, but we do recommend going as far as Camden, Maine which is about 1 1/2 hours from Portland each way.
  • Evening: Enjoy a sunset dinner on a rooftop terrace at Lobster Shack at Two Lights, featuring panoramic views of the city. Order their signature cocktails and a platter of fresh local oysters.

Final thoughts

Portland, Maine, with its charming combination of historic sites, vibrant culinary scene, and picturesque landscapes, offers a perfect weekend escape for anyone looking to immerse themselves in the unique culture and natural beauty of New England. Whether you're exploring the city's streets on a self-guided walking tour, indulging in the freshest seafood at a local eatery, or enjoying the serene views of the ocean, Portland promises an unforgettable experience. This guide has aimed to showcase the best of what Portland has to offer, from its culinary delights to its scenic spots, ensuring your visit is as enriching as it is enjoyable.

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Hi! We're Chris and Sara a husband and wife video making, storytelling, travel loving duo with a passion for sharing travel tips, tricks, and inspiration with others.
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