Portland, Maine, is a charming coastal city known for its rich history, vibrant arts scene, delicious seafood, and stunning natural beauty. This itinerary is divided into eight sections, each focusing on a different aspect of what makes Portland a unique and exciting destination.
Landmarks
Portland Head Light
Portland Head Light, located in Fort Williams Park in Cape Elizabeth, is one of the most iconic and photographed lighthouses in the United States. Established in 1791, it offers stunning views of the rugged Maine coastline and the Atlantic Ocean. Visitors can explore the surrounding park, which includes walking trails, picnic areas, and historical ruins. The museum inside the lighthouse keeper’s quarters provides fascinating insights into the lighthouse’s history and operation.
Victoria Mansion
Victoria Mansion, also known as the Morse-Libby House, is a beautifully preserved 19th-century mansion located in downtown Portland. This Italianate-style house, built in 1860, features exquisite interiors with original furnishings, intricate woodwork, and stunning stained glass windows. Guided tours offer a glimpse into the opulent lifestyle of the Victorian era and the mansion’s historical significance.
Eastern Promenade
The Eastern Promenade is a scenic park that stretches along the eastern edge of the Portland peninsula. This historic park offers panoramic views of Casco Bay, the Calendar Islands, and the Portland skyline. Visitors can enjoy walking and biking trails, picnic areas, and access to East End Beach. The Eastern Promenade is also home to Fort Allen Park, which features historical monuments and a bandstand.
Food and Cuisine
Eventide Oyster Co.
Start your culinary journey in Portland with a visit to Eventide Oyster Co., a renowned seafood restaurant known for its fresh oysters and innovative dishes. The oyster selection features varieties from both the East and West Coasts, served with unique accoutrements. Don’t miss the famous brown butter lobster roll, a modern twist on a classic Maine dish. The menu also includes delicious crudos, chowders, and other seafood delights.
The Holy Donut
For a sweet treat, head to The Holy Donut, famous for its potato-based donuts. These unique donuts are made with Maine potatoes, resulting in a moist and flavorful texture. Flavors range from classic glazed and cinnamon sugar to creative options like maple bacon, pomegranate, and chocolate sea salt. The Holy Donut also offers gluten-free and vegan options, ensuring there’s something for everyone.
Fore Street
For an upscale dining experience, visit Fore Street, a farm-to-table restaurant located in the Old Port district. The menu features seasonal dishes made with locally sourced ingredients, including fresh seafood, meats, and vegetables. Highlights include wood-roasted mussels, pan-seared scallops, and spit-roasted pork loin. The restaurant’s rustic, open-kitchen setting adds to the warm and inviting atmosphere.
Duckfat
No visit to Portland would be complete without a meal at Duckfat, a popular eatery known for its Belgian-style fries cooked in duck fat. These crispy, golden fries are served with a variety of dipping sauces, including truffle ketchup and garlic aioli. The menu also features delicious panini sandwiches, poutine, and milkshakes. Duckfat’s casual yet trendy vibe makes it a favorite among locals and visitors alike.
Entertainment
Portland Stage
Portland Stage is the city’s premier professional theater company, offering a diverse range of productions throughout the year. The theater’s season includes classic plays, contemporary works, and world premieres. The intimate setting and high-quality performances make for a memorable night out. Check the schedule to see what’s playing during your visit and enjoy a captivating live performance.
State Theatre
The State Theatre is a historic venue in downtown Portland that hosts a variety of live music and entertainment events. From indie bands and rock concerts to comedy shows and film screenings, the State Theatre offers something for everyone. The beautifully restored interior and excellent acoustics make it a top destination for live entertainment in Portland.
Portland Symphony Orchestra
The Portland Symphony Orchestra (PSO) is one of the most respected regional orchestras in the United States. The PSO performs a wide range of classical and contemporary music, including symphonies, chamber music, and pops concerts. Performances are held at the Merrill Auditorium, a beautiful concert hall with excellent acoustics. Check the PSO’s schedule for upcoming concerts and experience the magic of live orchestral music.
Culture
Portland Museum of Art
The Portland Museum of Art (PMA) is the largest and oldest public art institution in Maine. The museum’s collection includes over 18,000 works of art, ranging from American and European paintings to contemporary art and decorative arts. Highlights include works by Winslow Homer, Andrew Wyeth, and Claude Monet. The museum also hosts rotating exhibitions, educational programs, and special events. The PMA’s beautiful building and sculpture garden make it a must-visit for art lovers.
Wadsworth-Longfellow House
The Wadsworth-Longfellow House is the childhood home of the famous American poet Henry Wadsworth Longfellow. Located in downtown Portland, this historic house museum offers guided tours that provide insights into the life and work of Longfellow and his family. The house is beautifully preserved, with original furnishings, family artifacts, and period decor. The adjacent Longfellow Garden is a peaceful oasis in the heart of the city.
Space Gallery
Space Gallery is a contemporary art space that showcases visual arts, performances, film, and music. Located in the heart of Portland, Space Gallery features rotating exhibitions by local, national, and international artists. The gallery also hosts artist talks, workshops, and community events. Space Gallery’s mission is to promote and support contemporary art and artists, making it a vital part of Portland’s cultural scene.
Outdoor Activities
Casco Bay Islands
The Casco Bay Islands, also known as the Calendar Islands, are a group of islands located just off the coast of Portland. Visitors can take a ferry from the Portland waterfront to explore these beautiful islands, each with its own unique charm. Popular islands include Peaks Island, known for its biking and walking trails; Great Diamond Island, home to Fort McKinley; and Chebeague Island, offering quiet beaches and scenic views. Activities include hiking, biking, kayaking, and picnicking.
Eastern Promenade Trail
The Eastern Promenade Trail is a scenic multi-use trail that runs along the waterfront, offering stunning views of Casco Bay and the surrounding islands. The trail is perfect for walking, jogging, biking, and bird-watching. Along the way, you’ll find picnic areas, playgrounds, and access to East End Beach. The trail also connects to the Back Cove Trail, providing even more opportunities for outdoor recreation.
Portland Observatory
The Portland Observatory, located on Munjoy Hill, is the last remaining maritime signal tower in the United States. Built in 1807, the observatory offers panoramic views of Portland, Casco Bay, and the surrounding area. Visitors can take guided tours to learn about the history of the observatory and its role in Portland’s maritime history. The climb to the top is well worth it for the breathtaking views.
Shopping
Old Port
The Old Port district is the heart of downtown Portland and a shopper’s paradise. This historic area is characterized by its cobblestone streets, 19th-century brick buildings, and charming storefronts. The Old Port is home to a diverse mix of boutiques, art galleries, specialty shops, and bookstores. Popular stops include Portland Trading Co., a curated shop featuring clothing and home goods, and Sherman’s Books & Stationery, Maine’s oldest bookstore. The Old Port also offers a variety of dining options, from casual cafes to fine dining restaurants.
Portland Flea-for-All
For a unique shopping experience, visit Portland Flea-for-All, an indoor marketplace featuring vintage, antique, and handmade goods. Located in the Bayside neighborhood, the Flea-for-All is open on weekends and offers a diverse selection of items, including furniture, clothing, jewelry, and artwork. The market is a great place to find one-of-a-kind treasures and support local artisans.
L.L. Bean
A visit to Portland wouldn’t be complete without a trip to the L.L. Bean flagship store in nearby Freeport. This iconic outdoor retailer is known for its high-quality clothing, footwear, and outdoor gear. The flagship store is open 24 hours a day, 365 days a year, and features a wide range of products, including camping equipment, fishing gear, and hiking boots. Freeport’s charming downtown area also offers a variety of outlet stores, boutiques, and restaurants.
History
Maine Historical Society
The Maine Historical Society, located in downtown Portland, is dedicated to preserving and sharing the state’s rich history. The society’s museum features rotating exhibits on Maine’s history, culture, and people. The adjacent Wadsworth-Longfellow House offers guided tours that provide insights into the life of Henry Wadsworth Longfellow and his family. The Longfellow Garden is a peaceful oasis in the heart of the city. The Maine Historical Society’s library and archives are also open to the public, offering resources for genealogical and historical research.
Portland Observatory
The Portland Observatory, built in 1807, is the last remaining maritime signal tower in the United States. Located on Munjoy Hill, the observatory offers panoramic views of Portland, Casco Bay, and the surrounding area. Visitors can take guided tours to learn about the history of the observatory and its role in Portland’s maritime history. The climb to the top is well worth it for the breathtaking views.
Tate House Museum
The Tate House Museum, located in the Stroudwater neighborhood, is a beautifully preserved 18th-century Georgian house. Built in 1755 for Captain George Tate, a British mast agent, the house offers guided tours that provide insights into the colonial history of Portland and the lives of the Tate family. The museum features original furnishings, period decor, and a beautiful garden. The Tate House Museum is a fascinating glimpse into Portland’s colonial past.
Beaches
Crescent Beach State Park
Crescent Beach State Park, located in Cape Elizabeth, is a popular destination for beachgoers and nature lovers. The park features a mile-long crescent-shaped beach with soft sand and gentle surf, making it ideal for swimming, sunbathing, and picnicking. Visitors can also explore the park’s walking trails, which wind through wooded areas and offer scenic views of the coastline. The park is open year-round and offers amenities such as restrooms, picnic tables, and a snack bar.
Willard Beach
Willard Beach, located in South Portland, is a small, family-friendly beach with stunning views of Casco Bay and the surrounding islands. The beach is popular with locals and offers a relaxed atmosphere, perfect for swimming, beachcombing, and picnicking. Willard Beach also has a playground, restrooms, and a snack bar, making it a convenient spot for a day at the beach. Nearby, the Spring Point Ledge Lighthouse and Fort Preble provide additional opportunities for exploration.
Higgins Beach
Higgins Beach, located in Scarborough, is a picturesque beach known for its fine white sand and excellent surfing conditions. The beach is popular with surfers, fishermen, and beachcombers, who enjoy searching for sand dollars and other treasures. The remnants of a shipwreck can often be seen at low tide, adding to the beach’s unique charm. While there are no lifeguards on duty, the beach is a great spot for a peaceful day by the ocean.
Festivals and Events
Old Port Festival
The Old Port Festival is one of Portland’s most popular annual events, celebrating the city’s vibrant arts and culture scene. Held in June, the festival features live music, food vendors, art exhibits, and family-friendly activities. The streets of the Old Port district come alive with performances, street vendors, and a parade. The festival is a great way to experience the energy and creativity of Portland’s community.
Maine Brewers’ Guild Summer Session
Maine is known for its craft beer scene, and the Maine Brewers’ Guild Summer Session is a must-attend event for beer enthusiasts. Held in July, this beer festival features over 100 beers from more than 50 Maine breweries. Attendees can sample a wide variety of brews, including IPAs, stouts, and sours, while enjoying live music and food from local vendors. The festival takes place on the Portland waterfront, offering stunning views of Casco Bay.
Harvest on the Harbor
Harvest on the Harbor is Portland’s premier food and drink festival, celebrating the city’s culinary scene. Held in October, the festival features a series of events, including tastings, cooking demonstrations, and competitions. Highlights include the Maine Lobster Chef of the Year competition, the Maine OysterFest, and the Market on the Harbor, where attendees can sample and purchase local food and beverages. Harvest on the Harbor is a delicious way to experience the best of Portland’s food and drink culture.
Portland, Maine offers a wealth of experiences for travelers, from its rich history and cultural attractions to its stunning natural beauty and vibrant entertainment scene. Whether you’re exploring landmarks, indulging in delicious cuisine, or enjoying outdoor activities, this itinerary provides a comprehensive guide to making the most of your visit to this charming coastal city.