Outbound Collective logo

Ipswich, Massachusetts

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

Top Chillin Spots in and near Ipswich

  • Ipswich, Massachusetts

    Photograph Castle Hill

    4.0
    Castle Hill refers to either a 165-acre drumlin surrounded by sea and salt marsh or to the mansion that sits on the hill. Both are part of the 2,100-acre Crane Estate located on Argilla Road in Ipswich, Massachusetts.Take a walk through the public garden or down to the beach. Plenty of beautiful ...
    Read more
  • Boston, Massachusetts

    Freedom Trail

    4.7
    2.9 mi / 121 ft gain
    Park along the trail and then hop on. The Freedom Trail allows you to not only see the most beautiful parts of Boston (which is an absolutely gorgeous city) but you can learn some history too! Head off the trail a bit to explore the Charles River, the waterfront near the aquarium and picturesque ...
    Read more
  • Hull, Massachusetts

    Explore the Bunkers at Fort Revere

    Fort Revere is an 8-acre (3.2 ha) historic site situated on a small peninsula located in Hull, Massachusetts. It is situated on Telegraph Hill in Hull Village and contains the remains of two seacoast fortifications, one from the American Revolution and one that served 1898-1947. There are also a ...
    Read more
  • 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...
    Read more
  • Acton, Massachusetts

    Hike the Pratt's Brook Conservation Area Loop

    4.0
    1.5 mi / 85 ft gain
    Park in the small parking area right before the trailhead. *Notice this parking area is small and only fits about 3-4 cars so prepare to find street parking on a busy day. You can punch in the coordinates to a GPS if you need help finding it: 42.4545482, -71.4358192.  The loop is very diverse wit...
    Read more
  • 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....
    Read more
  • Groton, Massachusetts

    Catch a Sunset at Gilbert Hill

    5.0
    1 mi
    From Rt. I-495 Exit 31, Gibbert Hill has one of the greatest sunsets around Groton, MA area. You will see a lot of cows and even a castle. This is a very easy hike and a not so easy place to park, you have to leave you car on the side of the road, which is totally fine, I guess, it is easy.The wa...
    Read more
  • 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...
    Read more
  • Bolton, Massachusetts

    Take a Stroll at Fyfeshire Conservation Area

    1.0
    Fyfeshire is located in Bolton Massachusetts off "Wattaquadock Hill Road", near the "Fotini's Restaurant and Bar". The trailhead begins at a small parking area with a stone gate that says Fyfeshire Conservation area on a wood plank. Once you are in the conservation area you will see an opening in...
    Read more
  • Clinton, Massachusetts

    Watch a Sunset at Wachusett Reservoir

    4.5
    Wachusett Reservoir is located in central Massachusetts, northeast of Worcester. Easy location and parking, you can go anytime of the day and you won't be disappointed. The Reservoir is the second largest body of water in the State of Massachusetts, taking place in 5 cities around the area, West ...
    Read more
  • 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...
    Read more