Welcome to the picturesque seaside town of Portland, Maine! Whether you crave fresh seafood, adore outdoor activities, or just want a peaceful weekend escape, Portland presents a unique allure. Boasting a lively cultural scene, age-old elegance, and breathtaking natural vistas, this town by the Atlantic beckons as the ideal spot for a noteworthy weekend journey. In this weekend overview, we’ll guide you to both must-see landmarks and lesser-known treasures, ensuring your Portland trip is remarkable.
Day 1: Exploring the Heart of Portland
Morning: Breakfast at Holy Donut
Start your day with a sweet treat at Holy Donut, a local favorite known for their unique potato-based donuts.
Visit the Old Port District
After your delicious breakfast, take a stroll through the historic Old Port district. Don’t forget to stop by the iconic Portland Head Light for some fantastic photo opportunities.
Lunch at DiMillo’s on the Water
For lunch, head to DiMillo’s on the Water, a floating restaurant that offers fresh seafood and spectacular views. Try their famous clam chowder or indulge in a lobster roll while you dine aboard a converted car ferry.
Afternoon: Discover the Arts Scene
Portland is known for its thriving arts scene, and a visit to the Portland Museum of Art is a must.
Catch a Show at Cross Insurance Arena
In the evening, be sure to catch a show at the Cross Insurance Arena. Whether it’s a concert, sporting event, or live performance, the arena hosts a variety of entertainment options. Check the schedule ahead of time to see what’s happening during your visit.
Dinner at Street and Co.
Wrap up your day with a memorable dinner at Street and Co., a cozy restaurant known for its Mediterranean-inspired seafood dishes. The seafood stew and lobster fra diavolo are highly recommended. Make a reservation in advance to secure a table.
Day 2: Exploring the Outdoors
Morning: Sunrise at Fort Williams Park
Start your day early with a visit to Fort Williams Park. It’s not just any park—it’s home to the famous Portland Head Light, one of the most photographed lighthouses in the world. Arrive before sunrise to witness the breathtaking beauty of the coastline as the first light of day graces the historic lighthouse.
Breakfast at Becky’s Diner
After your sunrise adventure, refuel with a hearty breakfast at Becky’s Diner. This classic diner is known for its friendly atmosphere and delicious comfort food. Try the blueberry pancakes or the traditional eggs benedict.
Explore the Casco Bay Islands
Portland is the gateway to the Casco Bay Islands, and a day trip to some of these islands is a fantastic way to spend your afternoon. You can take a ferry to Peaks Island, Great Diamond Island, or Little Diamond Island, each offering its own unique charm. Explore the island villages, rent a bike, or simply relax on the beaches.
Lunch on an Island
While on the island, savor a seafood lunch at one of the local restaurants. Many of them offer fresh lobster rolls and other delicious dishes with a waterfront view.
Afternoon Adventure: Kayaking or Stand-Up Paddleboarding
For those seeking an active adventure, consider renting a kayak or stand-up paddleboard to explore the pristine waters of Casco Bay. You’ll have the chance to paddle alongside marine life and experience the stunning coastal scenery up close.
Dinner at Fore Street
Return to the mainland for a memorable dinner at Fore Street. This renowned restaurant specializes in farm-to-table cuisine, featuring locally sourced ingredients. The wood-fired dishes, including the roasted Maine mussels and grilled hanger steak, are sure to delight your taste buds.
Day 3: Hidden Gems and Local Delights
Morning: Coffee and Pastries at Tandem Coffee Roasters
Start your day with a visit to Tandem Coffee Roasters, a local gem known for its artisanal coffee and delectable pastries. The welcoming atmosphere makes it a great spot to relax and plan your day.
Hidden Gem: Eastern Promenade
Many visitors overlook the Eastern Promenade, a peaceful waterfront park that offers stunning views of Casco Bay and the surrounding islands. Take a leisurely walk along the Eastern Prom Trail and enjoy the fresh sea breeze.
Lunch at Duckfat
For lunch, head to Duckfat, a popular eatery famous for its Belgian-style fries fried in duck fat. Pair them with a gourmet panini or a hearty soup for a satisfying meal.
Visit the Portland Observatory
Explore the history of Portland by visiting the Portland Observatory, a historic maritime signal tower. Climb to the top for panoramic views of the city and the harbor, and learn about its role in guiding ships safely into port.
Afternoon: Brewery Tour
Portland is known for its thriving craft beer scene. Take an afternoon brewery tour and sample some of the finest local brews. Some notable breweries to consider visiting include Allagash Brewing Company, Shipyard Brewing Company, and Bissell Brothers Brewing Co.
Dinner at Central Provisions
End your weekend with a delightful dinner at Central Provisions. This trendy restaurant offers small plates meant for sharing, allowing you to savor a variety of flavors. Their creative cocktails and seasonal dishes are a perfect way to cap off your Portland experience.
Additional Tips for Your Portland Weekend Getaway
Local Seafood: While in Portland, don’t miss the opportunity to indulge in the freshest seafood. Lobster, clam chowder, and oysters are local specialties you must try.
Shopping: Portland is a shopper’s paradise with its boutique shops, art galleries, and antique stores. Explore Exchange Street and the Old Port for unique finds.
Water Activities: If kayaking or paddleboarding isn’t your thing, consider taking a scenic boat tour to explore the coastline and spot local wildlife.
Cultural Events: Check the local events calendar for festivals, art exhibitions, and live music performances that may be happening during your visit.
Accommodation: There are plenty of charming bed and breakfasts, boutique hotels, and waterfront accommodations in Portland. Book your stay in advance to secure your preferred lodging.
Portland, Maine, offers a perfect blend of natural beauty, cultural richness, and delicious cuisine. Whether you’re savoring a lobster roll by the waterfront, exploring hidden gems, or enjoying a live performance at Cross Insurance Arena, your weekend getaway in this coastal gem will be a memorable experience. Embrace the relaxed pace of life, and let Portland’s charm captivate your heart. Enjoy your adventure in this picturesque New England city!
