15 Best Things to Do in Westfield (MA)

In the rolling hills of western Massachusetts, the city of Westfield is where the Berkshires meet the Connecticut River Valley

In recent times Westfield has emerged as a craft beverage hotspot, with a whole roster of breweries for beer connoisseurs to hit up.

A long-standing tradition of philanthropy has left the city with some top-notch attractions. One is Stanley Park, with a sequence of manicured display gardens, an arboretum and duck pond.

The generosity of the local couple, Amelia and Albert Ferst, has also left Westfield with a state-of-the-art ice rink and a new building for its superb children’s museum.

1. Stanley Park

Open to the public free of charge from May to November, Stanley Park is the kind of outdoor attraction any city would be proud of.

This isn’t actually a public park, as it’s owned by a non-profit foundation established by the businessman Frank Stanley Beveridge (1879-1956).

Set on the north bank of the Little River, Stanley Park contains an arboretum, a patchwork of gardens including a magnificent rose garden, a 98-foot carillon tower, a range of sports facilities, a blacksmith shop, kidscape, pavilions, a wildlife sanctuary and a great deal more.

Possibly the most treasured feature is the duck pond, supporting a rare diversity of waterfowl and equipped with special feed-dispensing machines.

2. Amelia Park Children’s Museum

The philanthropic couple, Albert (1919-2011) and Amelia Ferst (1920-1997), have left a lasting legacy in Westfield.

Next to Westfield Middle School, on the south side of downtown you’ll find Amelia Park, which has a memorial garden, an NHL-size rink and the Amelia Park Children’s Museum.

Albert Ferst put $1m towards the new, 12,000-square-foot building for this attraction, which was completed in 2008.

The museum is filled with hands-on exhibits for experiential learning, like the Dinosaur Dig, Outer Space playground, Construction Zone, Toddler Area, Wellness Center, STEM Center, Grocery Store, Amelia’s Café and a newly redesigned library area with dozens of brand new books.

3. Columbia Greenway Rail Trail

In Westfield, a former spur of the New York, New Haven and Hartford Railroad cutting through downtown is now a multi-use rail trail, opening in phases.

When we compiled this article the Columbia Greenway Rail Trail began at Main Street, running south as far as the town line with Southwick where it merges with the Southwick Rail Trail.

The trail is unique, as the old line is elevated for its entirety through downtown. At the time of writing a bridge was being constructed on Main Street, and the final phase will connect downtown with Women’s Temperance Park on the north bank of the Westfield River.

4. Grandmother’s Garden

A short way west of downtown Westfield is Allen Park, which was donated to the city by one Albert Allen in 1929 to be used as a park.

This included a formal garden on a half-acre plot, in memory of Albert’s mother and designed by local horticulturalist Elizabeth Bush Fowler (1886-1954).

Over time this became known as Grandmother’s Garden, and this space owes its survival to the non-profit organization, Friends of Grandmother’s Garden (F.O.G.G.), which was set up when the garden was threatened with closure in 1994.

With a cute pavilion and a riot of color in summer, Grandmother’s Garden is a favorite setting for wedding and family photographs, or a little me time with a book.

5. Hampton Ponds State Park

In the very northeast of Westfield there’s a chain of ponds with a recreation area on the southeast side.

Hampton Ponds State Park is a delight in summer for its two clean and large sandy beaches, one of which is guarded.

You’ve also got a newly renovated boat ramp, and both motorized and non-motorized vessels are permitted.

After some swimming or paddling you can relax with a picnic or cookout, courtesy of the charcoal grills here. When it comes to fishing, Hampton Ponds are stocked in spring and fall with trout, while largemouth bass, sunfish and chain pickerel have all been caught here.

6. Westfield Farmers’ Market

On Thursday afternoons from early June to late October there’s a farmers’ market in an attractive setting next to the Episcopal Church of the Atonement on Court St.

When we put this article together there were more than 20 full-time vendors, and a large contingent of part-time and visiting vendors.

Shopping at the market you can look forward to super-fresh local fruit and vegetables, fresh roasted coffee, maple syrup, pickles, herbs, cut flowers, honey, breads, pastries, pasture-raised meat & poultry, jams, balms, handmade soaps, jewelry, candles, lotions, and much more than we can list here.

7. Westfield River Walk

On the north side of downtown Westfield there’s a 1.7-mile trail on the banks of the Westfield River, all within a block or two of the center’s restaurants.

The parking lot for the trail is just next to the Great River Bridge, and you’ll never be more than a few steps from the closest park where you can stop for a picnic or just enjoy the peace for a moment.

From the parking lot you can head east in the direction of Chapman’s Playground, go upstream towards Whitney Field, or cross the footbridge to Women’s Temperance Park and Half Mile Falls Park.

8. Bearhole Reservoir

In the shadow of East Mountain just across the line in West Springfield there’s a reservoir that was built in 1907 and is framed by majestic scenery, with interesting history to boot.

From around the 1870s until this became a watershed, it was the site of the Bear Hole Resort, the main attraction being a three-legged black bear kept in a caged den.

On the 2.6-mile marked trail looping around the reservoir you can still see the grand fireplace from the old restaurant, sitting close to a scenic cascading waterfall that is at its best in early spring or after a long rainy spell.

9. Amelia Park Arena

Also part of the Fersts’ legacy in Westfield is the city’s only ice rink, a 47,000-square-foot facility that opened to the public in 2000.

The Amelia Park Arena houses an NHL-size rink and seating for 600 spectators. If you want to catch a game, this is home ice for the Westfield State Owls, who play in the NCAA Division III.

Extra amenities include a party room, a figure skating lounge, a food concession area, skate rental and sharpening and four locker rooms.

Check the website for details of public skate, freestyle and stick and puck sessions, as well as programs to learn to skate and learn to play hockey. Outside is a 65’x170′ rink for street hockey, with glass around the boards, LED lighting and a scoreboard.

10. Skyline Beer Company

What began as a homebrewing hobby more than 20 years ago became the Skyline Hop Shop in 2014, and within a few more years this had become the ten-barrel brewery, tasting room and 4,500-square-foot restaurant open today.

Skyline Beer Company has 20 beers on tap at any time, and on “One-Off Wednesday” the brewery taps a five-gallon, one-off release.

A few of the core beers usually available are Wobbly Boots Mile 1 (IPA), Sunday Drive (New Zealand Pilsner), Noble View (Pilsner), B-Berry (Blueberry Wheat Ale), Skyline Trail (Lager) and Irish Goodbye (Stout).

For accompaniment you’ve got pretzels, dips, flatbreads, salads and a wide choice of baked-to-order cookies. There’s also live music, trivia nights, yoga sessions and occasional visits from food trucks.

11. Robinson State Park

Overlapping into Westfield but mostly in Agawam, this 1,025-acre state park hugs the south bank of the Westfield River for five miles.

The sudden elevation changes at Robinson State Park give rise to an unusual variety of tree and plant species, with a fabulous assortment of wildflowers blooming in late spring and summer.

Despite the rough topography, this is an easy park to navigate as there’s a long paved road tracing the river through most of the park, while scenic trails primed for mountain biking weave along the ridges and offer some surprising views.

The park was founded in 1934, and preserves several buildings erected by the Civilian Conservation Corps (CCC).

12. Tin Bridge Brewing

This craft brewery has an unprepossessing spot, next to a liquor store at the Little River Plaza Shopping Center in the east of Westfield.

Step inside the low, long and narrow building and you’ll find yourself in a rustic and welcoming taproom.

Open Thursday to Sunday, Tin Bridge Brewing has new releases by the week, and there’s a rotating selection of NEIPAs, Hazy Ales, Sours and maltier brews.

One long-term favorite is the Peanut Butter Porter. There’s almost always a food truck outside, for lobster rolls, BBQ, pizza, burgers and the like, and you can normally catch live music on Fridays and Saturdays.

13. Great Awakening Brewing Company

Fans of great beer are in for a treat in Westfield as there’s another craft brewery in town. Great Awakening Brewing Company opened in 2020 at the beautiful old Mill at Crane Pond, and has a lovely pond-side beer garden with a view of the mill’s dam on the Little River.

Remarkably there are 32 beers on tap here, whether you’re in the mood for malty Stouts, hop-forward IPAs, crisp and fruity Sours and Saisons, or simple classics like a Pilsner, Lager or Brown Ale.

Great Awakening has its own kitchen, with an exciting menu tailored for beer. Think flatbread pizza, charcuterie boards, dill pickle dip and pulled pork mac and cheese.

14. Tekoa Mountain

This prominent peak looms dramatically over the north bank of the Westfield River in neighboring Russell and Montgomery.

Tekoa Mountain isn’t strictly a mountain, but rather a cleaver, a glacial formation jutting from a dissected plateau at the boundary between the Berkshires and the Connecticut River Valley.

This was the logical starting point for the Jacob’s Ladder Trail, an early automobile tourist route, which we’ll talk about below.

If you’re up for the challenge you can scramble up the crags and boulders to the summit on a looping, unmarked hike, starting at Tekoa Road and taking around four hours.

15. Jacob’s Ladder Trail Scenic Byway

Starting at the Westfield/Russell town line, U.S. Route 20 becomes a scenic byway, winding westwards for 30 miles through the southern Berkshires beside the Westfield River.

The Jacob’s Ladder Trail opened in 1910, becoming the first highway built specifically for automobiles and dubbed the “the First of the Great Mountain Crossovers”.

The 1920s marked the height of the trail’s popularity, which subsided with the Great Depression and the completion of the Massachusetts Turnpike.

By staying off the beaten track, the byway has held onto its rural character, and offers many of the same sights and panoramas that greeted drivers in the 1910s and 1920s.

If you plan to stop at the natural spaces along the route it could take days to complete the journey, with breathtaking waterfalls, stupendous mountain vistas, 180-year-old railway bridges and a trailhead for the Appalachian Trail.