If you had to pick a small town to sum up New England, Glastonbury on the east bank of the Connecticut River would come close.
The town is flush with beautiful colonial-era houses, some going 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.
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, shuttling 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.
When it comes to recreation, Riverfront Park has spaces for lacrosse and soccer, as well as a floodlit baseball field and a basketball court.
You may prefer just to idle by the water and watch the lazy river and its traffic drift by.
On the water you’ll find a public boat launch, as well as boat storage facilities and the genteel Glastonbury Boathouse, which is rented out for weddings and events.
There’s a fenced-in 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
Glastonbury has five distinct historic districts, each furnished with architecture going back at least as far as the early 18th century.
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 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, and the adjacent Green Cemetery was established in 1693, at a time when Main Street was an Indian Trail.
3. Apple Harvest & Music Festival
Glastonbury celebrates its apple harvest in style with a three-day festival attracting more than 23,000 people to Riverfront Park in mid-October.
Going back to the 1970s, the Apple Harvest & Music Festival has three stages of live music, a midway packed with amusement rides, more than 100 vendors, some 25 food trucks/stalls and 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 17th year in 2019. All runners aged 21 and up will 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.
As of July 2019 the ferry runs April 1 to November 30, from 07:00 to 18:45 (Tuesday to Friday) and 10:30 to 17:00 on weekends.
Tickets for vehicles cost $5, while pedestrians and cyclists can cross for $2. This is one of just two regular ferries over the Connecticut River, and during the ten-minute trip you can appreciate the broad river and its wo
oded 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, raised in 1840 and serving for 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.
You’ll get the background on former Glastonbury manufacturers, like Harriman Motors, a giant in aviation in the early 20th century.
A riveting exhibit tells the story of the Smiths of Glastonbury (a mother and her five daughters), early champions of abolition, women’s rights and education at the turn of the 19th 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 picture-perfect set of falls, with three distinct channels plunging over the rocks.
If there’s an ideal time to make the trip it’s spring or after heavy rainfall, as the falls can be little more than a trickle at the height of summer.
From here you can plot a longer excursion up the Blackledge River into Gay City State Park.
7. 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 a homestead and purpose-built in the early-1950s on the site of the home of its benefactors, Harriet Welles and Sturgis P.
For anyone just visiting Glastonbury, the library is also a handy resource, providing free maps, newspapers, free Wi-Fi, computer banks and restrooms.
8. Dondero Orchards
Here since 1911, Dondero Orchards runs a community supported agriculture programme, 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, and 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.
Every other Wednesday in summer there are Farm Dinners, for proper homemade meals alfresco, serving Italian food (twice), steaks, BBQ, a clam bake and an Autumn Harvest feast to round off the season.
9. 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 and its crop of Sangiovese, Cabernet Franc, Cabernet Sauvignon, Vignoles and Chardonnay 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, 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 programme of live music at the winery in summer.
10. 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 Tuesday to Sunday 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 hay ride.
On Sunday mornings from June to October there’s Breakfast with a View, serving berry-laden waffles, pancakes, French toast and more at the farm’s deck, which is perched on an overlook.
The farm also runs a stand at 1200 Hebron Avenue, stocked with seasonal produce like berries, peaches, herbs, flowers, cucumber, lettuce, peppers, spinach, apples, pears and lots more, as well as home-baked pies, salad dressings, salsas, teas, honey and decorations.
11. Webb-Deane-Stevens Museum
The largest historic district in Connecticut is just across the river in Wethersfield.
You could make the crossing and go back in time at the Webb-Deane-Stevens Museum, composed 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, with wood panelling, 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, with an upper floor 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, with a rich assemblage of decorative arts from the end of the 17th century.
12. Minnechaug Golf Course
This well looked after nine-hole par 35 municipal course sits at the foot of east Glastonbury’s Minnechaug Mountain.
A round at Minnechaug Golf Course culminates 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.
Green fees are more merciful at $18 and $19 (weekends) for non-residents.
At the ninth hole there’s a menu for the course restaurant, Giovanni’s Pizzeria so you can call ahead and your order will be ready when you are.
13. Central Rock Gym
This chain of indoor climbing centres has several locations in the Northeast, and the only one 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 2100 square metres of climbing terrain, up to 12 metres high and comprising 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 classes, both on the walls and off at the yoga studio and fitness centre.
14. 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 on Tuesdays in July and August.
You’ll be greeted by a guide in period costume and will be shown around the interiors, which feature what is thought to be the largest period fireplace in Connecticut.
There’s also a herb garden, 300-year-old loom, spinning wheels, tobacco shed and a 19th-century English-style bank barn filled with lots of interesting implements and tools.
15. 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, and the brook 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 is restricted to Glastonbury residents except for fishing between the third Saturday of April and June 15.