Glastonbury, Connecticut: Best Things to Do – Top Picks

Getting to Glastonbury

Glastonbury is conveniently located in central Connecticut, just 10 miles southeast of Hartford. The town is easily accessible by car via Interstate 84 and Route 2, making it a straightforward journey from major Northeast cities. If you’re flying in, Bradley International Airport is approximately 25 miles away, offering numerous domestic and international connections.

Best Time to Visit Glastonbury

Glastonbury shines throughout the year, but each season offers unique experiences. Summer (June-August) brings warm temperatures perfect for outdoor activities along the Connecticut River. Fall (September-November) transforms the landscape with spectacular foliage colors, making it ideal for scenic drives and hiking. The Apple Harvest & Music Festival in October is a highlight, drawing over 25,000 visitors. Spring (April-May) offers pleasant weather and blooming landscapes, while winter (December-February) creates a quintessential New England atmosphere with occasional snowfall.

1. Riverfront Park: Scenic Recreation Hub

Glastonbury’s Riverfront Park stands as the town’s premier outdoor destination, offering stunning views of the Connecticut River from its strategic location on a scenic bend. This expansive park combines natural beauty with excellent recreational facilities, making it perfect for visitors of all ages and interests.

The park features multiple sports fields for lacrosse and soccer, a floodlit baseball diamond, and basketball courts for active visitors. Families appreciate the separate playgrounds designed for different age groups, while dog owners can take advantage of the fenced dog park area. The expansive open fields and picnic areas make it ideal for relaxing afternoons by the water.

Water enthusiasts will find the public boat launch and the elegant Glastonbury Boathouse particularly appealing. The boathouse, which can be rented for special events, provides a picturesque backdrop for weddings and gatherings. Riverfront Park is also known for hosting community events throughout the year, including the popular Apple Harvest & Music Festival each October.

2. Glastonbury Historic District: Step Back in Time

The Glastonbury Historic District offers a captivating glimpse into New England’s past with its well-preserved colonial architecture and historic sites. Located along Main Street between Hebron Avenue and Talcott Road, this 128-acre district contains 81 historic buildings, including 23 houses built before 1800, with some dating back to the 17th century.

Walking through the district reveals a spectrum of architectural styles, from Colonial and Greek Revival to Queen Anne. The Town Green serves as the heart of the historic area, providing a peaceful spot to rest while absorbing the historical atmosphere. Adjacent to the Green, you’ll find the Green Cemetery, established in 1693 when Main Street was still a Native American trail.

The Historical Society of Glastonbury, housed in the former Town Hall (a Greek Revival building from 1840), offers fascinating exhibits on the town’s Native American heritage, colonial history, and industrial development. The museum is free to visit and open on Mondays, Tuesdays, Thursdays, and the third Sunday of each month.

3. Apple Harvest & Music Festival: Autumn Celebration

Every October, Glastonbury celebrates its agricultural heritage with the vibrant Apple Harvest & Music Festival at Riverfront Park. This three-day event has been a town tradition since the 1970s and now attracts more than 25,000 visitors who come to enjoy live music, delicious food, and family-friendly activities.

The festival features three stages of live music spanning various genres, creating a lively atmosphere throughout the weekend. Over 100 vendors and 25 food trucks offer everything from apple-inspired treats to local crafts. The popular Harvest Pub, which has expanded in recent years, serves a selection of regional beers and ciders for adults to enjoy.

On Sunday, the Angry Orchard 5K road race adds a sporty element to the festivities, with participants aged 21 and up receiving a complimentary pint of Angry Orchard cider at the Harvest Pub after completing the run. With amusement rides, artisan demonstrations, and activities for all ages, the Apple Harvest & Music Festival perfectly captures Glastonbury’s community spirit and fall charm.

4. Rocky Hill-Glastonbury Ferry: Historic River Crossing

Experience a piece of living history aboard the Rocky Hill-Glastonbury Ferry, which has been in continuous operation since 1655, making it the oldest ferry service in the United States. This essential transportation link connects Glastonbury and Rocky Hill across the Connecticut River, saving travelers up to 13 miles of detour when operational.

The ferry operates from April 1 to November 30, running weekdays from 7:00 AM to 6:45 PM and weekends from 10:30 AM to 5:00 PM. Passengers board the Hollister III, an open flatboat hauled across the river by a towboat, for a charming 10-minute journey that offers beautiful views of the river and its wooded banks. Lucky travelers might even spot eagles soaring overhead.

As one of only two regular ferries crossing the Connecticut River, this historic service provides not just transportation but a unique experience that connects visitors to the region’s past. The ferry accommodates both pedestrians and vehicles, making it a practical and enjoyable way to cross between the two communities.

5. Historical Society of Glastonbury: Preserving Local Heritage

The Historical Society of Glastonbury offers visitors an immersive journey through the town’s rich past. Housed in the former Town Hall, a stately Greek Revival building from 1840, the museum showcases a diverse collection of artifacts and exhibits spanning from pre-colonial Native American culture through the industrial boom era.

Exhibits highlight significant aspects of Glastonbury’s development, including its colonial settlement, participation in the Civil War, and industrial achievements. Particularly fascinating are the displays about former local manufacturers like Harriman Motors, which played a crucial role in early 20th-century aviation history.

The Society also maintains the Welles-Shipman-Ward House in South Glastonbury, a 1755 Colonial mansion featuring what is believed to be Connecticut’s largest period fireplace. This historic home, open for tours in spring and summer, includes a herb garden, 300-year-old loom, and a 19th-century English-style bank barn filled with antique farming implements.

6. Natural Attractions: Outdoor Exploration

Blackledge Falls

Located on the Glastonbury-Hebron town line, Blackledge Falls offers a perfect blend of adventure and accessibility. This 80-acre nature preserve features a light trail just over a mile long that leads to a picturesque waterfall with three distinct channels cascading over rocky outcrops. The falls are most impressive during spring or after heavy rainfall, though they remain beautiful even when reduced to a gentle trickle in summer.

Cotton Hollow Preserve

For those seeking a more rugged hiking experience, Cotton Hollow Preserve offers 80 acres of woodland trails along the fast-flowing Roaring Brook. The preserve contains fascinating ruins of a cotton mill dating back to 1814, providing glimpses into the area’s industrial past. The combination of rushing water, historic ruins, and dense forest creates a uniquely atmospheric hiking destination.

7. Farms and Orchards: Agricultural Experiences

Dondero Orchards

Operating since 1911, Dondero Orchards offers visitors the chance to connect with Glastonbury’s agricultural traditions through pick-your-own fruit experiences from May through October. The seasonal progression begins with strawberries, followed by early Lodi apples, pears, peaches, blueberries, raspberries, plums, and nectarines. Apple season runs from August through October, with 12 varieties available for picking, from early Baldwins to late Russets.

Rose’s Berry Farm

Rose’s Berry Farm delights visitors with its extensive pick-your-own berry options, including strawberries, raspberries, blueberries, and blackberries during summer months. In autumn, the farm transforms with a pumpkin patch and hayrides that are especially popular with families. Their farm stand at 1200 Hebron Avenue offers fresh seasonal produce, homemade pies, teas, and specialty items like house-made salsas.

A highlight at Rose’s Berry Farm is their “Sunday Breakfast with a View” event, where visitors can enjoy a delicious morning meal while taking in panoramic views of the farm’s rolling hills. This unique dining experience runs from mid-June through early October, offering a perfect way to start a day of exploration in Glastonbury.

8. Crystal Ridge Winery: Local Wine Tasting

Nestled among the rolling hills of south Glastonbury, Crystal Ridge Winery offers visitors a taste of Connecticut’s growing wine scene. This family-run boutique winery, established in 2004, cultivates Sangiovese, Cabernet Franc, Cabernet Sauvignon, Vignoles, and Chardonnay grapes on its 200-acre estate, taking advantage of the rocky soils and sunny, southwest-facing slopes.

The winery’s tasting room, which opened in 2018, welcomes visitors to sample their well-reviewed selection of varietal wines while enjoying spectacular views that extend to the Hartford skyline on clear days. The relaxed atmosphere makes it an ideal spot to unwind after a day of exploring Glastonbury’s attractions.

During summer months, Crystal Ridge enhances the visitor experience with a program of live music events. Check their website for the current schedule of performances, which provide the perfect backdrop for enjoying their wines in the picturesque setting of the vineyard.

Where to Stay in Glastonbury

Glastonbury offers several comfortable accommodation options for visitors, from modern hotels to charming bed and breakfasts. The Hilton Garden Inn and Homewood Suites provide convenient lodging near The Shops at Somerset Square, offering easy access to dining and shopping. For those seeking a more intimate experience, local inns and vacation rentals can be found throughout the town, many within walking distance of the historic district.

Dining in Glastonbury

Glastonbury’s dining scene has flourished in recent years, with upscale restaurants from Hartford and the Farmington Valley establishing locations in town. Visitors can enjoy a diverse range of culinary experiences, from fine dining to casual eateries and farm-to-table establishments that showcase local produce.

Popular dining spots include Bricco Trattoria for Italian cuisine, Max Fish for seafood, Plan b Glastonbury for gourmet burgers, and First & Last Tavern for classic American fare. For wine enthusiasts, Bin 228 Wine Bar & Gastropub offers an excellent selection of wines paired with Mediterranean-inspired dishes. Many restaurants are concentrated in Glastonbury Center and along Main Street, making it easy to find dining options while exploring the town.

Getting Around Glastonbury

Having your own vehicle provides the most flexibility for exploring Glastonbury and its surrounding attractions. The town is spread across 52 square miles, with points of interest distributed between Glastonbury Center, South Glastonbury, and East Glastonbury. Major roads like Main Street (Route 17) and Hebron Avenue make navigation straightforward.

For those without a car, limited public transportation options are available. The town offers Dial-A-Ride services for seniors and those with disabilities. Taxi services and rideshare apps can also be used for point-to-point transportation. When visiting the historic districts, particularly in Glastonbury Center and South Glastonbury village, many attractions are within walking distance of each other.

Practical Tips for Visitors

Nearby Attractions

While Glastonbury offers plenty to keep visitors engaged, several noteworthy attractions lie just beyond its borders. The Webb-Deane-Stevens Museum in neighboring Wethersfield presents a fascinating look at colonial life through three historic houses from the 1700s, including the Joseph Webb House where George Washington once stayed.

Hartford, just across the Connecticut River, provides additional cultural experiences with attractions like the Mark Twain House, Wadsworth Atheneum Museum of Art, and the Connecticut Science Center. For outdoor enthusiasts, the surrounding region offers numerous hiking trails, state parks, and scenic drives, particularly beautiful during fall foliage season.

Experience the Charm of Glastonbury

Glastonbury, Connecticut offers visitors a delightful blend of historical exploration, natural beauty, and modern amenities. From the scenic banks of the Connecticut River to the rolling hills dotted with farms and orchards, this quintessential New England town provides authentic experiences that connect travelers to America’s past while offering contemporary comforts.

Whether you’re sampling local wines at Crystal Ridge Winery, picking seasonal fruits at historic farms, exploring the town’s colonial architecture, or enjoying the natural splendor of Blackledge Falls, Glastonbury rewards visitors with memorable experiences throughout the year. Plan your visit to discover why this charming Connecticut town has been captivating travelers for generations.