Road.Travel Road.Travel
    7 Activities

    Fascinating Day Trip to Portland

    Fascinating Day Trip to Portland
    Starts from

    Boston

    Transportation

    By Car

    Guidance

    Self-Guided

    Activities

    7

    Duration

    9 hours

    Length

    66 mi

    Guide details

    Starts from

    Boston

    Transportation

    By Car

    Guidance

    Self-Guided

    Duration

    9 hours

    Length

    66 mi

    Natural AttractionsGastronomy
    Map preview
    Kelsey Perrett

    Kelsey Perrett

    Travel Expert

    • Sample sweets in Perkins Cove and Old Orchard Beach.
    • Lunch on the waterfront of adorable Kennebunkport, ME.
    • Stroll Congress Street through the heart of downtown Portland, ME.
    Portland, ME, a hip and artistic city on the Casco Bay, may be the perfect day trip destination. A scenic coastal drive, great shopping, and great food are the highlights of this journey.
    This road trip visits the traditional lands of the Wabanaki, Aucocisco, Abenaki, Pequawket, Pennacook, and Pentucket peoples. Travel in the warmer months, when shops are open and outdoor activities are at their most pleasant.

    Categories

    Portland, ME, a hip and artistic city on the Casco Bay, may be the perfect day trip destination. A scenic coastal drive, great shopping, and great food are the highlights of this journey.
    This road trip visits the traditional lands of the Wabanaki, Aucocisco, Abenaki, Pequawket, Pennacook, and Pentucket peoples. Travel in the warmer months, when shops are open and outdoor activities are at their most pleasant.
    Kelsey Perrett

    Kelsey Perrett

    Travel Expert

    • Sample sweets in Perkins Cove and Old Orchard Beach.
    • Lunch on the waterfront of adorable Kennebunkport, ME.
    • Stroll Congress Street through the heart of downtown Portland, ME.

    Day Itinerary

    7 Activities
    Map preview

    Day 1

    66 mi0.7 mi

    Taking Coastal Cruise to Portland, ME

    Head up the coast to Portland, one of the best day trip options. On the way, you'll stop through the stunning beach towns of southern Maine, including Ogunquit, Kennebunkport, and Old Orchard Beach.
    Portsmouth Love Wall
    10:1545 min

    Portsmouth Love Wall

    Other Great Outdoors
    Open Details
    There’s a lot to love about Portsmouth, NH. So if you find yourself strolling through the city struck by Cupid’s arrow, pay a visit to the “Love Wall” in Prescott Park. This chain-link fence above the parking area is adorned with padlocks symbolizing eternal love — an homage to the Pont des Arts “Love Lock” bridge in Paris. The tradition is to write your name on the lock and toss the key into the Piscataqua River, but be cool and don’t litter.
    16.9 mi
    25 min
    Marginal Way
    11:301 hr 30 min

    Marginal Way

    Promenade
    Open Details
    Perkins Cove, or simply “The Cove” is a historic fishing and arts community that has embraced the summer tourist scene with a collection of walkable shops and restaurants.
    Leave your car at the start of the Marginal Way, an about one-mile paved oceanside path from Ogunquit, ME. The drawbridge and the basin dock make great photo opportunities, but there’s also a great candy store for the sweet tooth in your car.
    11.9 mi
    25 min
    Alisson's Restaurant
    13:301 hr 30 min

    Alisson's Restaurant

    Restaurant
    Open Details
    Stop for lunch in the adorable riverfront town of Kennebunkport, ME. This quaint harbor is a tourist darling, with some quality restaurants to boot. Alisson’s Restaurant on Dock Square is a star among stars with an easygoing vibe. Expect traditional seafood and pub fare with a few wacky twists. You haven’t really experienced Kennebunkport until you try the lobster pizza.
    18.3 mi
    30 min
    15:305 min

    Parking Lot

    Parking
    Open Details
    Leave your car in this parking lot, and head to the beach for some fun in the sun.
    0.2 mi
    5 min
    Old Orchard Beach Pier
    15:4530 min

    Old Orchard Beach Pier

    Pier
    Open Details
    Stretch your legs with a stroll around the boardwalk of Old Orchard Beach. There is a lively lineup of beachfront bars and restaurants where you can snack or drink with your toes in the sand, while the Palace Playland amusement park bustles with carnival vibes in the summertime. Wander out the Old Orchard Beach fishing pier to drink in the full experience.
    18.8 mi
    30 min
    Portland Museum of Art
    16:451 hr

    Portland Museum of Art

    Museum
    Open Details
    The Portland Museum of Art in Congress Square is the heart and soul behind Portland’s funky, artsy atmosphere. Here, at the largest and oldest public art institution in the state of Maine, you’ll find the works of acclaimed painters like Winslow Homer, Andy Warhol, and Claude Monet. Visitors can also indulge in more contemporary exhibitions in the free outdoor sculpture park and surrounding Portland Arts District.
    0.6 mi
    10 min
    Central Provisions
    18:001 hr 30 min

    Central Provisions

    Restaurant
    Open Details
    Portland, ME, has such a wealth of great dining establishments that it's tough to label them with superlatives like "best" or "most popular." But if one had to narrow it down, Central Provisions would certainly be high on that list. This intimate brick space (formerly a storehouse for The East India Trading Company) serves small plates and snacks on a rotating menu. They also have an extensive wine list, so be sure to ask for a pairing! Reservations are recommended and can be made on the official website.
    Map preview
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