Winthrop, Maine
Looking for the best chillin in Winthrop? We've got you covered with the top trails, trips, hiking, backpacking, camping and more around Winthrop. The detailed guides, photos, and reviews are all submitted by the Outbound community.
Top Chillin Spots in and near Winthrop
-
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 -
Rumford, Maine
Hike Black Mountain Resort
3.1 mi / 1312.3 ft gainStart at parking-place, make it to the top and chose a route to hike back down. Beautiful views lay in front of you, for you to enjoy. This is a half day hike, full of nice places on the way to have lunch at, or just to enjoy and walk by. Enjoy the Hike ;)Read more -
Weld, Maine
Tumbledown Mountain via Brooke Trail
5.06.33 mi / 2238.41 ft gainTo keep the hike as short as possible, the hike can be an out and back at 5.6 miles, but if you wanted to make it a loop that is possible and adds only an additional 2 miles or so. We took the Brook Trail up to the summit (which passes by the alpine lake) and then followed it back down. To hike t...Read more -
Byron, Maine
Swim in Coos Canyon
5.0Coos Canyon is right off of route 17 in Byron, ME. It's almost impossible to miss but if you're worried about it you can type "coos canyon" or "coos canyon rock and gift" into google maps and it will take you right there. There is a gravel parking lot to the right side of the road (heading north)...Read more -
Denmark, Maine
Summit Bald Peak and Mt. Pleasant
6 mi / 1450 ft gainAfter 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 ...Read more -
Portland, Maine
Kayak Casco Bay
4 miThis 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 -
Camden, Maine
Hike Mount Megunticook in Camden Hills State Park
2.9 mi / 1000 ft gainAfter 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 -
Phillips, Maine
Smalls Falls
Smalls Falls stands out as one of Western Maine's most accessible and spectacular waterfall destinations. The site combines natural beauty with family-friendly accessibility, making it a perfect stop for travelers along Route 4 or a dedicated destination for waterfall enthusiasts. The unique geol...Read more -
South Portland, Maine
Portland Breakwater Lighthouse (Bug Light)
5.0Built 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 -
South Portland, Maine
Spring Point Lighthouse
4.71 mi / 39 ft gainBeing 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 -
Portland, Maine
Hike to Jewell Falls
4.52 mi / 300 ft gainFore 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 -
Cape Elizabeth, Maine
Portland Head Light
5.0Portland 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 -
Newry, Maine
Photograph Screw Auger Falls
3.50.2 mi / 6 ft gainAfter parking in the allotted parking area at screw auger, make your way down to the falls to explore! There are several "smaller waterfalls" that the river flows over before making its way to the 27 foot main attraction. Going in April, the falls were at their most powerful. It made taking pictu...Read more -
Monhegan, Maine
Explore Monhegan Island
4.4 mi / 538 ft gainNearly 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