15 Best Things to Do in Glastonbury (CT)

If I had to pick a perfect small town to sum up the best of New England, Glastonbury on the east bank of the Connecticut River would come close.

The town is flush with beautiful colonial-era houses. Some of these go back to the 17th century, and its main Historic District is on a classic town green.

Travel south and you’ll be in rolling hills coated with deciduous woodland, orchards and berry farms. I don’t need to tell you that the colors in fall are out of this world.

Every October, the Apple Harvest & Music Festival is a roaring success, attracting tens of thousands to the town’s Riverfront Park over three days.

And crossing the CT River is what is believed to be the oldest operating ferry service in the United States. The ferry shuttles between Glastonbury and Rocky Hill for seven months of the year.

Let’s explore the best things to do in Glastonbury:

1. Riverfront Park

The newest park in Glastonbury is also the best equipped, with a gorgeous location on a bend in the Connecticut River. It’s also the best place in town to watch the sun go down.

When it comes to recreation, Riverfront Park has spaces for lacrosse and soccer, as well as a floodlit baseball field and a basketball court. I would come here just to idle by the water and watch the river traffic drift by.

On the water you’ll find a public boat launch, as well as boat storage facilities and the genteel Glastonbury Boathouse. This space can be rented out for weddings and events.

There’s a fenced park for dog walkers, separate playgrounds for infants and bigger kids, large open fields, picnic areas, and a pavilion for shelter.

2. Glastonbury Historic District

The town has five distinct historic districts, each furnished with architecture going back to the early 18th century and before. For me it’s a quaint slice of New England, and well worth a drive.

On Main Street you can’t miss the Glastonbury Historic District, set between Hebron Avenue and Talcott Road. Over these 128 acres there are 23 houses built before the 1800s, several of which date from the 17th century.

Among the 81 buildings there’s a spectrum of styles, among them Colonial, Greek Revival and Queen Anne.

On the Town Green you can dip into the town’s past at the Historical Society of Glastonbury. Meanwhile the adjacent Green Cemetery was established in 1693, at a time when Main Street was a Native American trail.

3. Apple Harvest & Music Festival

Glastonbury celebrates its apple harvest in style with a three-day festival attracting more than 25,000 people to Riverfront Park in mid-October.

Going back to the 1970s, the Apple Harvest & Music Festival has three stages of live music across the event. There’s a midway packed with amusement rides, as well as more than 100 vendors, and some 25 food trucks/stalls. I’ve got to mention the much-loved Harvest Pub, which is now bigger than ever.

On the Sunday, one of the main events is the Angry Orchard 5K road race, a fun run in its 20th-year when I was here. All runners aged 21 and up can quench their thirst with a free pint of Angry Orchard cider at the Harvest Pub.

4. Rocky Hill-Glastonbury Ferry

What is thought to be the oldest continually operating ferry service in the United States has crossed the Connecticut River between Glastonbury and Rocky Hill since 1655.

South of Connecticut Route 3 there isn’t a single crossing on the river until you get to Middletown. So the ferry remains a much-needed transport link for seven months of the year, saving detours of up to 13 miles.

You’ll board the Hollister III, an open flatboat, hauled across the river by a towboat.

When I was here the ferry ran from April 1 to November 30, from 7:00 AM to 6:45 PM (Monday to Friday) and 10:30 AM to 5:00 PM on weekends.

This is one of just two regular ferries over the Connecticut River. During the ten-minute trip you can appreciate the broad river and its wooded banks, and may get to see an eagle overhead.

5. Historical Society of Glastonbury

In the stately streetscape of the Glastonbury Historic District sits the former Town Hall. This Greek Revival building was raised in 1840 and served the town for a hundred years.

This is now the home of the Historical Society of Glastonbury’s free museum, open Monday, Tuesday and Thursday, and the third Sunday of the month.

You can examine a wealth of historic objects starting with the pre-colonial Native Americans and continuing through the colonial period, Civil War and the industrial boom days when shipbuilding and manufacturing dominated the local economy.

I was also thrilled to get the background on former Glastonbury manufacturers. An important one was Harriman Motors, a giant in aviation in the early 20th century.

6. Blackledge Falls

An adventure with all the convenience of a walk in the park, Blackledge Falls lies in 80 acres of lush deciduous woods on the Glastonbury-Hebron town line.

On a light trail, little more than a mile long, you’ll arrive at a picture-perfect set of falls. This has three distinct channels plunging over the rocks, and is maybe my favorite natural attraction in the area.

If there’s an ideal time to make the trip it’s during spring or after heavy rainfall. At the height of summer the falls can be little more than a trickle, but still extremely picturesque.

From here you can plot a longer excursion up the Blackledge River into Gay City State Park.

7. Dondero Orchards

Here since 1911, Dondero Orchards runs a community supported agriculture program, providing baskets of seasonal produce for people in the area.

But you can also come in person to pick-your-own fruit between May and the end of October. In chronological order there are strawberries (greenhouse then field), Lodi apples, pears, peaches, blueberries, raspberries, peaches, plums and nectarines.

Then in August, apple season begins in earnest. Over the next eight weeks some 12 varieties from the early-season Baldwins to the late Russets, will be ripe for picking.

Dondero Orchards also has a farm stand and bakery, for delectable pies, sauces, pickles and jams.

On certain Wednesdays in summer there are Farm Dinners on the farm, with a changing menu throughout the season.

8. Crystal Ridge Winery

This 200-acre estate in the south of Glastonbury, rests on rambling hills among fruit farms and woodland.

On a boutique scale and run by a family, Crystal Ridge Winery was founded in 2004. There’s a crop of Sangiovese, Cabernet Franc, Cabernet Sauvignon, Vignoles and Chardonnay that flourishes in the rocky soils of these sunny, southwest-facing slopes.

The tasting room opened in 2018 and pours a well-reviewed choice of varietal wines. To my mind, these are best enjoyed as you gaze at the Hartford skyline off in the distance.

Stay up to date with Crystal Ridge’s website as there’s a program of live music at the winery in summer.

9. Rose’s Berry Farm

In summer and autumn Rose’s Berry Farm is also a must for fresh produce, growing tons of fruit and vegetables from May to October.

The main location on Matson Hill Road is open in summer for you to pick your own strawberries, raspberries, blueberries and blackberries. In autumn the pumpkin patch is ready, and kids will have a great time on the hayride.

The farm also runs a stand at 1200 Hebron Avenue. This is stocked with all kinds of seasonal produce, from berries to peppers. I can’t get enough of the specialty items here, like home-baked pies, teas, and salsas.

When I compiled this list, the farm had just changed hands to the Gondek family, who were keen to keep the old traditions going.

10. Webb-Deane-Stevens Museum

The largest historic district in Connecticut is just across the river in Wethersfield. I would definitely make the crossing to go back in time at the Webb-Deane-Stevens Museum.

This enthralling historical attraction is made up of three refined houses from the 1700s, all in a row.

The Joseph Webb House and Silas Deane House here have been returned to their mid-18th-century appearance. These boast wood paneling, contemporaneous furniture, portraits, and plasterwork.

The Joseph Webb House was George Washington’s headquarters in 1781, while Silas Deane was the first foreign diplomat to France from the United States.

The Isaac Stevens House, home of a middle class leatherworker, dates to 1789 and has been kept as it was in the 1820s and 30s. The upper floor is dedicated to childhood in this period and replete with dolls and antique toys.

Another property, the Buttolph Williams House (1711) is also managed by the museum and found close by. Inside is a rich assemblage of decorative arts from the end of the 17th century.

11. Minnechaug Golf Course

This nine-hole par 35 municipal course sits at the foot of east Glastonbury’s Minnechaug Mountain. My round at Minnechaug Golf Course culminated with two exciting challenges.

The eighth hole is a 126-yard par 3 onto an island green, thought to be the first of its kind in New England, and one of the first in the United States.

The ninth is another unforgiving par 3, at 158 yards with nothing but water between the tee and green.

I’m happy to say the rates are more merciful, at less than $30 for 18 holes (weekdays) for non-residents when I played.

At the ninth hole there’s a menu for the course restaurant, the Tenth Hole Tavern so you can call ahead and your order will be ready when you are.

12. Central Rock Gym

Primed for lead climbing, top-roping, and bouldering, this chain of indoor climbing centers has several locations in the Northeast. One of only two to be found in Connecticut is right here in Glastonbury.

A spectacular mass of vertical walls and overhangs, Glastonbury’s Central Rock Gym has more than 22,600 square feet of climbing terrain. This stands up to 40 feet high and comprises 120 stations.

If you’re a first-timer you can phone ahead to book a one-hour belay tutorial (after signing a waiver). After that, a day pass will give you access to the gym’s walls.

To take your skills and conditioning to the next level there’s a range of programs. These take place both on the walls and off, at the yoga studio and fitness center.

13. Welles-Shipman-Ward House

If your interest in the area’s history is undimmed, the Historical Society of Glastonbury takes care of another beautiful house at 972 Main Street in the South Glastonbury Historic District.

The Welles-Shipman-Ward House is a Colonial mansion from 1755, open for tours in the spring and summer months.

On special events you’ll be greeted by a guide in period costume to be shown around the interiors. My highlight is what is thought to be the largest period fireplace in Connecticut.

There’s also a herb garden, 300-year-old loom, spinning wheels, and tobacco shed. I was especially intrigued by the 19th-century English-style bank barn, filled with interesting old farming implements and tools.

14. Cotton Hollow Preserve

On the rugged banks of the fast-flowing Roaring Brook is 80 acres of woodland for hiking and fishing.

Some 200 years ago these banks were a hive of industry. The brook here drove grist mills, saw mills, a cotton mill, and iron foundries. You can still make out the ruins of that cotton mill, going back to 1814.

The downside for out-of-towners is that entrance to Cotton Hollow Preserve was restricted to Glastonbury residents when I wrote this list. That is except for fishing between the third Saturday of April and June 15.

15. Welles Turner Memorial Library

For the people of Glastonbury this local library is a pillar of the community, especially for those with kids.

All year, but especially during school breaks, there are book clubs, games, storytimes, movie screenings and a great deal more.

The library is a lovely building, designed like an old homestead and purpose-built in the early-1950s. Interestingly, it stands on the site of the home of its benefactors, Harriet Welles and Sturgis P. Turner.

For people like me just visiting Glastonbury, the library is also a handy resource. Like a mini visitor center, this provides free maps, newspapers, free Wi-Fi, computer banks, and restrooms.