Naples, Maine

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

Top Chillin Spots in and near Naples

  • 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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  • 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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  • Stow, Maine

    Rattlesnake Pool

    2.11 mi / 207 ft gain
    The best place to start your hike is from Route 113 near Gilead, head towards Stone House Road. This becomes Shell Pond Road. A few miles in, you'll find a gated area where you can park. This trail, and Rattlesnake Pool, are both on private land - so be sure to practice leave no trace principles. 
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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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  • 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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  • Bartlett, New Hampshire

    Hike Cathedral Ledge

    4.0
    3.4 mi / 722 ft gain
    During spring, summer and fall there is a road that allows you to drive to the top of Cathedral Ledge. In winter the road is closed off to vehicles so reaching the top requires a 1.7 mile hike. Once at the top, there is a fenced in lookout with a 180 degree view of North Conway and the surroundin...
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  • 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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  • Jackson, New Hampshire

    Jackson Falls

    Jackson Falls is located In the village of Jackson, New Hampshire. This waterfall is easily accessible from the nearby parking area. The parking area has a 2-hour time limit, so make sure you check your watch before heading to the falls.  The falls drop 100' over a series of smaller cascasdes wi...
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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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  • 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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  • Albany, New Hampshire

    Rocky Gorge Scenic Area Loop

    2 mi / 266 ft gain
    A beautiful area of the Kancamagus Highway, the Rocky Gorge section is home to rushing rapids and scenic lakes. When visiting in the fall the colors are amazing however be ready for traffic and more crowds. This location has a parking lot and walking trails along the river to multiple viewpoints. 
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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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  • 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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  • Jackson, New Hampshire

    Drive Mt. Washington Auto Road

    3.0
    Starting at roughly 3,000ft above sea level the Mt. Washington Auto Road will take you up nearly eight miles of beautiful, scenic, and well maintained mountain auto roads to The Mount Washington Summit. The summit sits at 6,289 and offers stunning 360° views of New Hampshire's Presidential Range,...
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  • Gorham, New Hampshire

    Snowshoe to Carter Notch Hut

    7.8 mi / 2200 ft gain
    The nineteen mile brook trail is a winding path up approximately 2200 feet of elevation over the course of 3.9 miles. That distance feels a lot farther when you are breaking trail in 18-24 inches of snow and you are carrying 35 lb packs on your backs.  Luckily we started out early and we able to ...
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