Outbound Collective logo

Southport, Maine

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

Top Chillin Spots in and near Southport

  • 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...
    Read more
  • 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...
    Read more
  • 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...
    Read more
  • 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...
    Read more
  • 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...
    Read more
  • 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...
    Read more
  • 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...
    Read more
  • 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...
    Read more
  • Camden, Maine

    Hike Mount Megunticook in Camden Hills State Park

    2.9 mi / 1000 ft gain
    After driving in to Camden Hills State Park, there is a fork where you can go straight (to the campgrounds) or left (to head up Mount Battie). Take a left and then park in the parking lot immediately on your right. That is the trailhead to Mount Megunticook! The trail itself winds through the tre...
    Read more
  • Old Orchard Beach, Maine

    Photograph Sunrise at the 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...
    Read more

Top Activities