Portland, Maine

Looking for the best chillin in Portland? We've got you covered with the top trails, trips, hiking, backpacking, camping and more around Portland. The detailed guides, photos, and reviews are all submitted by the Outbound community.

Top Chillin Spots in and near Portland

  • Portland, Maine

    Kayak Casco Bay

    4 mi
    This kayaking adventure begins at East End Beach at the Eastern Promenade in Portland. There is an easy boat launch zone if you have your own sea kayaks, but if you need to rent, Portland Paddle is right at the launch zone! It is $45 for 2 hours with a tandem sea kayak, which is what we opted for...
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  • South Portland, Maine

    Portland Breakwater Lighthouse (Bug Light)

    5.0
    Built in 1855, (also known as 'Bug Light') the lighthouse was used as a breakwater to the bustling harbor of Portland during the booming shipbuilding era during the World Wars.  The small size of the the breakwater eventually led to the lighthouse being decommissioned in 1943, but located in Bug...
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  • South Portland, Maine

    Spring Point Lighthouse

    4.7
    1 mi / 39 ft gain
    Being a less popular lighthouse out of the many in the greater Portland area, parking is easy and crowds are limited. Parking at Fort Prebble is ideal for a short walk to the lighthouse. Completed in 1897, off the shoreline of Fort Prebble, Spring Point is a unique lighthouse with huge importanc...
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  • Portland, Maine

    Hike to Jewell Falls

    4.0
    2 mi / 300 ft gain
    Fore River Sanctuary is 85 acres in the heart of Portland right off of Congress Street. It is a unique place where the river meets the ocean and creates a marshland landscape, which provides a plethora of opportunities to see wildlife (especially a great diversity of birds - waterfowl, herons, eg...
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  • Cape Elizabeth, Maine

    Portland Head Light

    5.0
    Portland Head Light is one of Maine's most iconic and picturesque lighthouses that offers stunning views year round. Located just about 15 minutes outside of Portland, Maine, it's the perfect place to go to watch an early winter sunset and enjoy some ocean views. To get to the light house, you wi...
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  • Cape Elizabeth, Maine

    Hike around Cape Elizabeth's Dyer Cove

    5.0
    1 mi
    If you venture to Cape Elizabeth, you may be lucky enough to see it in the dense fog that I was able to.You'll take a windy road near Portland, Maine surrounded by cute, quaint homes on either side down to the rocky coastline. Park in the designated parking area (very easy to spot as the road's e...
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  • Old Orchard Beach, Maine

    Old Orchard Beach Pier

    5.0
    Few things create a more dramatic scene for a sunrise than a pier spanning out into the water, and the one in Old Orchard Beach is pretty iconic. Normally the area is pretty packed, and it can be tough to find a parking spot (especially in the summer). But at sunrise, there is just you, the beach...
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  • Freeport, Maine

    Sport Clays in Freeport

    Try shooting a gun with L.L. Bean's Discovery Sporting Clay course. You can book courses in the morning or afternoon and will meet at a specified location (the range) where you will meet with the guide and other participants. You will be introduced to the sport of shooting a gun at artificial tar...
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  • Wells, Maine

    Hike to Laudholm Beach at Wells National Estuarine Reserve

    1.5 mi / 0 ft gain
    From the main parking area take the Beach Barrier Trail which takes you through several different types of environment; fields, forests, and marshland before reaching Laudholm Beach to further explore or take a dip.Walk the length of Laudholm Beach if you have time where barrier beaches protect a...
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  • Ogunquit, Maine

    Watch the Sunrise from the Marginal Way Trail

    5.0
    2 mi / 70 ft gain
    Park near the Oceanside Oarweed restaurant or any other public spots on the cove's peninsula. Marginal Way is a nicely paved 1.25 mile out and back path, perfect for a morning walk or run on the rocky coast. Catch fishermen, lobstermen, and recreational boats as they leave, or choose to sit at on...
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  • Denmark, Maine

    Summit Bald Peak and Mt. Pleasant

    6 mi / 1450 ft gain
    After turning on Mountain Rd, look for East Pinnacle Condominiums. The trailhead is about 0.1miles after that on the right between the telephone poles marked 49 and 50. There is a dirt parking lot to pull into.  Now on to the hike! This hike begins by heading straight uphill immediately, and you ...
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  • York, Maine

    Photograph Nubble Lighthouse

    4.8
    Officially named Cape Neddick Light, though more commonly known as Nubble Light, this lighthouse is part of the National Register of Historic Places and is a local favorite for photography. The lighthouse park is located just over the New Hampshire / Maine state line in New England, in York, ME....
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  • Monhegan, Maine

    Explore Monhegan Island

    4.4 mi / 538 ft gain
    Nearly 10 miles off the coast of Maine, Monhegan Island is accessible by your choice of three ferry lines. Each vary in terms of length of stay on the island and time spent on the water.  Be sure you do your research prior to reserving your tickets.  Below you can find more information : Monheg...
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  • Portsmouth, New Hampshire

    Relax at Prescott Park

    5.0
    Prescott Park is a waterfront park in Portsmouth, New Hampshire that is famous for its extensive flower gardens.  During the warmer months, visitors can enjoy the blooms of the annual and perennial beds, sit in the shade of the Japanese crabapple trees, and relax on the white benches along the pe...
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  • Conway, New Hampshire

    Drive the Kancamagus Highway

    4.8
    34.5 mi
    The Kancamagus Highway is designated an American Scenic Byway. It cuts through the White Mountains of New Hampshire. The highest point along the drive is 3000 feet. It is known as one of the best fall viewing areas in the country. If your interested there is also several campgrounds along thi...
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