Combining rugged beauty, maritime history, and a thriving culinary scene, the city of Portland is one of Maine’s shining stars. It showcases the best of New England and has a unique charm.
Situated on Casco Bay, Portland packs a punch with its walkable Old Port district, beautiful working waterfront, and historic neighborhoods. This small city, although the largest in the state, is a destination where you can sip craft cocktails in a t-shirt or flannel without judgment, or walk into a dive bar and become friends with some locals over blueberry-pie Jell-O shots.
If indulging in the best lobster roll you’ve ever had at a lighthouse perched on the Atlantic Ocean sounds appealing, then Portland is the place for you. However, lobster and ocean views are just the beginning of what this city has to offer.
Are outdoor activities your thing? Lace up your boots to explore the numerous hiking trails nearby. Are you a beach lover? Portland has you covered. Looking for cultural experiences? Check out the buzzing art scene. Whether you seek a weekend of superb eating and drinking or a couple of days focused on wellness, Portland can provide the escape you desire. It encapsulates Maine’s tagline, “The way life should be.”
Relaxed, friendly, and fun, Portland never disappoints. If you’re planning your first trip, here’s all you need to know.
When Should I Go to Portland?
Summer is peak season for Portland, with warmer temperatures ideal for outdoor pursuits. Expect to enjoy food-truck fare accompanied by local brews while tapping your foot to live music in vibrant venues. However, despite the spectacular summer weather in southern Maine, this season sees a significant influx of visitors, making accommodations pricier and the streets more crowded.
Portland charms in all seasons, although winter can be frigid and snowy. Yet, the snowflakes falling on the cobblestone streets of the Old Port create a charming atmosphere, perfect for cozying up with a hot drink in one of the city’s cocktail bars.
The shoulder season may be the sweet spot for visiting Portland, presenting fewer crowds and more budget-friendly accommodations in fall and spring. Leaf-peepers can delight in the beautiful autumn colors, while foodies can savor the annual Harvest on the Harbor festival held in late October or early November.
How Much Time Should I Spend in Portland?
Portland works well as a weekend escape. In just a couple of days, you can sample various restaurants, breweries, and museums. However, a stay of three to four days will alleviate feelings of being rushed while allowing for a comprehensive taste of the city. Whether you cover the essentials or enjoy a local hike, a sunset sailing trip in Casco Bay, or an afternoon in the local boutiques, you’ll surely want to return.
Is It Easy to Get In and Around Portland?
For maximum freedom and flexibility, consider driving to Portland. Street parking can be tricky, particularly downtown and in the Old Port, where a few paid parking garages are available. If you don’t mind walking a few blocks, finding a parking spot is possible, but you may need to circle around a few times.
Portland International Jetport is conveniently located just 2 miles from downtown. Alternatively, you can fly into Boston Logan International Airport and rent a car for the nearly two-hour drive north. Amtrak trains also reach Portland, allowing for picturesque travel along the coast.
With the Old Port as your base, many popular attractions and restaurants are within walking distance. Public transport is available for those without a car, thanks to the Greater Portland METRO service.
Top Things to Do in Portland
Eat, Eat – and Eat Some More
Portland has earned its reputation as a gourmet paradise. Classic diners serve comforting dishes like pancakes topped with wild Maine blueberries, while high-caliber chefs craft impressive meals across various cuisines.
To start your culinary journey, a lobster roll is a must. However, the dining options don’t end there; Portland offers everything from craft donuts to Southern barbecue, Greek, Asian, Mexican, and Puerto Rican cuisine, alongside food trucks and much more.
If you’re an oyster enthusiast, sampling fresh offerings from the Atlantic is essential. A visit to local favorites will yield memorable experiences.
Hop Aboard a Boat
The rugged coastline of Portland is best explored via boat. Sunset sails are particularly enchanting, providing stunning views of the coastal landscape.
Visit at Least One Lighthouse
A trek south to Cape Elizabeth introduces you to the historic Portland Head Light, operational since 1791. Here, you can explore the on-site museum and wander the trails for picturesque views of this iconic landmark.
Hit Some Nearby Trails
Stretch your legs and enjoy nearby hikes. The 3.6-mile waterfront Back Cove loop trail offers views of the city. Alternatively, a short drive leads you to scenic state parks with trails that showcase Maine’s natural beauty.
My Favorite Thing to Do in Portland
I can’t get enough of the food and drink scene in Portland. Returning to favorite spots for cherished dishes while also trying out new restaurants and breweries each visit is part of the charm.
How Much Money Do I Need for Portland?
Budgeting for Portland can vary greatly. While dining out may be pricier than other areas, there are ways to experience the city without overspending. Focus on free activities and consider choosing budget-friendly meals for lunch to save for dinner and drinks.
Frequently Asked Questions about Portland
How Should I Pack for Portland?
Layering is key, regardless of the season. The weather can change quickly, so be prepared for varying temperatures throughout the day.
Do I Need to Make Advance Restaurant Reservations in Portland?
Yes, given its popularity as a foodie hub, advance reservation is highly recommended, especially during peak season.
How Much Should I Plan to Do in One Day or Weekend in Portland?
Avoid overplanning. Prioritizing quality experiences over quantity will enhance your trip, allowing you to truly savor Portland’s offerings.
