15 Best Things to Do in East Hampton (CT)

In rural East Connecticut, the town of East Hampton stands out for its many acres of public natural land.

In East Hampton’s state forests and state parks you can watch the epic Connecticut River rolling by, cross a 19th-century covered bridge and walk the course of a lost railroad that once shuttled passengers between New York and Boston in record time.

The Connecticut Valley is very fertile, and you can spend an afternoon in summer or fall picking your own fruit at the many farms.

On the water East Hampton has a captivating historic district dotted with Federal-style buildings at the site of a long lost river port.

1. Air Line State Park Trail

The ambitious New York, New Haven and Hartford Railroad got its name, Air Line, from the soaring viaducts built to ensure a level trackbed on its high-speed route from New York to Boston.

The Air Line opened in 1873 and the section between East Hampton and the Connecticut-Massachusetts linehad been abandoned by the mid-20th century to become a trail.

The 25-mile southern portion of this route, from East Hampton to Windham, is designated a National Recreation Trail and is a breeze to walk or cycle on.

The Air Line State Park Trail has a smooth stone dust surface and crosses buried 19th-century trestles at the Rapallo and Lyman viaducts, with benches positioned at scenic spots along the route.

2. Salmon River State Forest

A piece of the Air Line Trail carries you through the Salmon River State Forest, a haven for hiking, fly fishing and mountain biking, or just enjoying a picnic in nature.

The Salmon River is as placid as you can get today, but in the 19th century the banks were teeming with mills.

At North Westchester there were so many factories competing for waterpower that the grist mills had to run at night and the paper mill by day.

The Blue-Blazed Salmon River Trail snakes through the park, and takes you over an important piece of heritage, which we’ll cover next.

3. Comstock Covered Bridge

Spanning the Salmon River in the state forest is the last remaining covered bridge in East Connecticut.

Dating to 1840, it is one of only three crossings of its kind in the state and remains open to pedestrian traffic, although vehicles have been banned since the 1930s.

A decade before then, a truck crashed through the floor, and the ensuing renovation was carried out as a Depression-era employment initiative by the Civilian Conservation Corps.

The main bridge span is covered by a gabled roof, which has the benefit of protecting the timbers below from the weather, and slowing their ageing process.

4. Hurd State Park

There’s a stunning piece of the Connecticut River in East Hampton, where you can stroll down to the riverbank and take a family picnic in perfect seclusion.

At this point the river is more than 200 meters across, and if you happen to arrive at Hurd State Park by water in the summer months there’s a small campground reserved exclusively for people entering and leaving by boat.

The park spreads over more than 1,000 acres, and has a network of blazed trails streaking through the forest.

The orange and yellow trails take you to the top of the split rock, a set of granite ledges where you can see the river far below through the trees.

5. Lake Pocotopaug

The lake next to the namesake village in East Hampton is large by any standard, at just over 500 acres.

A lot of the residences at Lake Pocotopaug are year-round, although some are holiday rentals or second homes, so the population does swell a little in summer.

On the west shore is Sears Park, which has a little beach, but the recent presence of blue-green algae has ruled out swimming.

This beach is also restricted to residents and their guests.

For out-of-towners the best way to enjoy the lake passively is via Lake Drive, which bends around the west and north shore, affording spectacular vistas of Twin Islands and Scraggy Island on the water.

You can also rent a non-motorized vessel from Happiest Paddler, and we’ll talk about that later.

6. Fat Orange Cat Brew Co.

Craft breweries don’t get much more homespun than this small-batch seasonal brewery operating out of a barn in rural East Hampton.

Fat Orange Cat’s farm is on the Salmon River watershed, giving rise to the exceptionally pure water that goes into a range of brews including well-reviewed IPAS, sours, porters and more.

There’s plenty of outdoor seating and fire pits at the homey taproom, as well as outdoor heaters for a cosy time in the colder seasons.

You can opt for a flight of four glasses to sample a few beers at once, and pick up a few cans, which have beautiful illustrations.

7. Arrigoni Winery

Run by a family with more than a century of winemaking heritage, Arrigoni Winery is on 200 acres of fertile farmland set between the Connecticut River and Route 66. You can pause at the winery’s tasting room to sample some of Arrigoni’s 14 different varieties, made from estate-grown Merlot, Pinot Noir, Chardonnay, Riesling, Vidal Blanc and more.

There’s a lovely sunset patio and a covered pavilion with outdoor heaters and a fireplace for chilly evenings.

Choose from a classic or premium tasting (5 wines each), both of which come with a souvenir glass.

8. Middle Haddam Historic District

The quiet and rural waterfront area on the Connecticut River in East Hampton is worth checking out on a drive.

Between 1730 and 1880 this was a bustling river port, docked by ocean-going vessels and trading across the east coast of North America and the West Indies.

Mine Brook, which meanders through the village, was the site of a sawmill providing timber to a shipyard on the riverfront.

The Middle Haddam Historic District offers a perfect snapshot of the Federal period in Connecticut.

The majority of the 58 contributing buildings went up before 1835 and after the Revolutionary War, at a time when the shipyard and port were most active.

The buildings in the district from this period display a high degree of workmanship, which indicates the high number of skilled craftsmen in town at the time.

Two prime examples of Federal architecture are the stone-built Hurd Mansion (106 Moodus Road), for the eminent shipbuilder Jesse Hurd (1765-1831), and the smaller wood-frame dwelling across the road, built for his son-in-law at 97 Moodus Road in 1823.

9. Pumpkintown USA

For younger families, Pumpkintown USA is all about non-scary fun during the build-up to Halloween.

This attraction has a recreated post office, fire department, jail, barbershop, saloon and more, all populated by more than 70 cheerful pumpkinhead figures, as well as farmyard animals.

On weekends you can drop by for facepainting, a “Sling-a-Ding” game and a “Moonbounce Pumpkin”. A big part of any visit is the mile-long ride on the hay wagon, through woodland inhabited by more pumpkinheads going about their business in their rustic dwellings.

Finally, the Harvest Shop is stocked with seasonal goodies like maple syrup, fall plants, autumn fresh produce, pumpkin butter spreads and pumpkin spice-scented candles.

10. Day Pond State Park

One local body of water that does accept visitors is the picture perfect Day Pond, in 180 acres of public land.

The pond is named after the pioneering Day family, which impounded the pond to drive an up-and-down sawmill with a waterwheel.

Stone foundations hark back to that time, while the pond is stocked with trout which makes it a favored destination for anglers.

There’s a neat little beach area for swimming in the summer months and overlooking the water close by is a picnic pavilion, with more tables nearby on the east and west shores.

By the water you can step onto the Blue-Blazed Salmon River, which will lead you to the Comstock Covered Bridge on its south loop.

11. Brownstone Exploration & Discovery Park

The banks of the Connecticut River in Portland have a brownstone bedrock, which provided the building material for cities like New York, Portland, Philadelphia, Washington D.C. and Chicago.

The main quarry site was in operation from the 17th century until a flood and then a hurricane ended commercial quarrying in the 1930s.

Since the 2000s the flooded quarry has been transformed into a summer activity center with climbing walls, as well as paddleboards and kayaks for hire.

There’s also an inflatable obstacle course, wakeboarding, a rope swing and an amazing 11 different zip-lines.

12. Belltown Hill Orchards

In the north part of town and the neighboring communities the countryside is flush with fruit farms, many of which open up to the public for pick-your-own seasons in summer and fall.

June to the end of October, Belltown Hill Orchards has sweet and tart cherries, blueberries, plums, nectarines, peaches, pears, raspberries, apples (24 varieties) and pumpkins.

There’s a handy ripening calendar on the farm’s website and a guide to the many different types of apples, explaining storage, flavor, uses and texture.

All of this produce is available seasonally at the farm market, along with jams and jellies, salsas, soups, local honey, seasonal decorations and delectable baked goods like pies, brownies and apple cider donuts.

13. Gotta’s Farm and Cider Mill

In Portland, Gotta’s Farm and Cider Mill is in its fourth generation and was established in 1898. The farm has two locations, at Rte 17 for pick-your-own strawberries, peaches, pears and apples, and at the QP Farm Market on Rte 66. The latter sells farm-fresh fruit and vegetables, as well as enticing pies, breads and cookies, together with Christmas trees and decorations later in the year.

Gotta’s Farm also has a garden center, for annuals, hanging baskets, perennials, flowering shrubs, evergreens, herb plants and vegetable plants.

14. Happiest Paddler

For water activities on Lake Pocotopaug your best bet is this boating agency, just north of Sears Park on the west shore.

Happiest Paddler is open seven days in June, July and August, and is weather dependent in the transitional months.

For one hour, half a day or a full week you can rent kayaks or paddleboards (both single or double), as well as canoes and paddleboats (for two or four passengers.

Flotation equipment and paddles are included in the rental fee, so you’ll have all you need for a voyage around one of the largest lakes in the state.

15. Nike Missile Site HA-26 Launch Site

There’s something out of the ordinary hidden in the Meshomasic State Forest, on the edge of East Hampton in South Glastonbury and Portland, and slowly being swallowed by nature.

This is a long-abandoned radar and launch site for the Nike Ajax anti-aircraft missile.

This system was developed at the dawn of the Cold War, and the site was in service from 1956 to 1963. At Del Reeves Road on the Portland side of the line you’ll discover the IFC radar station, with the remnants of foundations, floor tiles, a flagpole and manholes to underground utilities.

At the launch site in South Glastonbury there are more faint vestiges, from stairs to the foundations of barracks and launch pits easily identified in the clearings.