Hikers trek along a stone path in a mountain valley. Trees flank the trail.

The Best Outdoor Adventures in Pioneer Valley

Pioneer Valley, Massachusetts is a picturesque and historically rich region that follows the Connecticut River as it winds through Hampden, Hampshire, and Franklin counties. The valley is home to the Five Colleges consortium—Amherst College, Hampshire College, Mount Holyoke College, Smith College, and the University of Massachusetts Amherst. 


Known for its vibrant blend of natural beauty, cultural institutions, and academic excellence, the area once played a key role in early American history and was a hotbed of abolitionist activity. Today, it offers a unique mix of small-town charm and intellectual energy, drawing residents and visitors with its scenic hiking trails, thriving arts scene, and progressive spirit.


While there are a plethora of museums and cultural centers in Pioneer Valley, there are also many outdoor adventures to be experienced as well. Keep reading to learn more about some of our favorite outdoor excursions in Pioneer Valley!

Wooden bridge arches over a path, leading into lush green forest.

Hiking

Whether you’re chasing summit views along the ridgelines or meandering along rivers and rail-rails, Pioneer Valley’s trails showcase a diversity of terrain and ecosystems. The region’s hiking network spans hundreds of miles and caters to every level of outdoor enthusiasm. A few to check out are:


  • Metacomet–Monadnock Trail / New England National Scenic Trail: This epic 114 mile trail traverses the spine of the Pioneer Valley, following the Metacomet Ridge across iconic peaks like Mount Tom, Mount Holyoke, and Mount Norwottuck. It includes sweeping cliff-top vistas, waterfalls, wetlands, and connects to the Robert Frost and Appalachian Trails. 
  • Mount Holyoke Range & Skinner State Park: Situated near Amherst and Hadley, this park offers a network of moderate to strenuous trails, highlighted by the steep, but rewarding, ascent of Bare Mountain via the Notch Visitor Center. Multi-use paths here are ideal for hiking, horseback riding, skiing, and snowshoeing. 
  • Arcadia Wildlife Sanctuary: Boasting roughly 4 miles of woodland and creek-side trails, including an accessible loop, this sanctuary is a local favorite for birding and nature strolls.
  • Chapel Falls & Two Bridges Trail: A scenic 2-mile hike that begins at Chapel Falls and winds through the forest, small bridges, and rushing water. Great for a half-day excursion.
  • Mount Sugarloaf State Reservation: Offering a short but steep climb, this trail rewards hikers with panoramic views over the Connecticut River Valley. 
  • Mount Greylock Bradley Farm Trail: An easy 1.8-mile loop, the trail passes through former agricultural land and its new forest succession. 
  • Rail‑Trail Routes (e.g., Southwick Rail Trail, Norwottuck Rail Trail, Springfield Reservoir Trail): Converted from old rail lines, these flat, paved trails span 6–7 miles and are perfect for hiking, biking, or in-line skating.

Water Activities

Whether you're in the mood for gentle sunset paddles, adrenaline-pumping rapids, or peaceful camping float trips, Pioneer Valley has a water adventure waiting for you. Here are some fantastic ways to enjoy the water in the Pioneer Valley:
Canoeing, Kayaking, and Paddleboarding

  • Pioneer Valley Riverfront Club: Offers kayaking, adult & youth rowing, and vibrant dragon boat teams. Open year‑round, all skill levels are welcomed.
  • Connecticut River Greenway State Park: Spans over 12 miles of shoreline with access ramps for canoes, kayaks, paddleboards, motorboats, and fishing.
  • Barton Cove: Near Turners Falls, this is a favorite spot for eagles, wildlife, peaceful waters, and seasonal full-moon or sunset paddles led by Guide outfitters like Adventure East.
  • Connecticut River Paddlers’ Trail: Offers primitive campsites and multiple launch points along the river for tranquil shoreline camping and extended paddles. 


Whitewater and Rafting Adventures

  • The Westfield River: A National Wild & Scenic tributary, the Westfield River provides over 50 miles of Class II whitewater, perfect for intermediate kayakers and thrill-seekers.
  • Franklin County: You’ll find rafting & zip-line experiences along the Westfield, plus the Westfield River Whitewater Races each April.
  • Charlemont: Zoar Outdoor offers top-notch whitewater rafting, guided kayaking trips, and paddlesports clinics for all ability levels.


Fishing

  • The Connecticut River: The Connecticut River and its tributaries support fishing, especially for trout and bass.
  • The Westfield River: Also known for its trout fishing, the Westfield River is a popular location for anglers. 
Person in an orange life vest paddles a canoe on a turquoise lake, mountains in the background.
Colorful hot air balloons against a blue sky with fluffy clouds.

Hot Air Ballooning

See the Pioneer Valley from a bird’s eye view by taking a hot air balloon ride high above the valley floor. Places like Misty River Ballooning offer lovely rides over Pioneer Valley and even include a champagne toast. 

Skiing and Snowboarding

In the winter, enjoy both skiing and snowboarding at the Jiminy Peak Mountain Resort. This is a popular location for winter sports and features private and group lessons.


The resort is also open during the summer with attractions such as the Mountain Adventure Park and Ariel Adventure Park. Mountain biking is available onsite as well. 

Where to Stay: The Old Mill Inn

After a full day of outdoor adventures, come back to The Old Mill Inn to relax and unwind. Enjoy our beautifully appointed rooms or suites with all the amenities you need to rejuvenate after a busy outing. You’ll love the chic, rustic feel of our property and our proximity to the waterfall and river. In fact, many of our rooms offer views of the water!


Whether you’re here for a weekend getaway, a class reunion, or just to enjoy the outdoors, we welcome you! Make your reservation at The Old Mill Inn today.