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Things to Do in Portland, CT: A Local Guide to the River Town

By Erik Hernal, founder & editor

The top things to do in Portland, CT are Brownstone Adventure Park (161 Brownstone Avenue), a flooded quarry rebuilt for cliff jumping and ziplines; the Arrigoni Bridge over the Connecticut River; Portland Riverfront Park (284 Brownstone Avenue); and the Air Line State Park Trail. Portland, Connecticut sits right across that bridge from Middletown, a small river town whose brownstone quarries built half the rowhouses in New York and Boston. There's also a brewery, a cidery, and good places to eat, all open and checked this month.

The big one: Brownstone Adventure Park

Brownstone Exploration & Discovery Park (161 Brownstone Avenue) is the reason most people first cross the bridge into Portland. It's a flooded brownstone quarry rebuilt into an adventure park: cliff jumping, ziplines over the water, wakeboarding, kayaking, scuba, and rock climbing, all in turquoise quarry water. It runs as a summer operation, weekends from late May and then seven days a week from Father's Day through Labor Day, so it's a warm-weather plan, not a year-rounder. Buy timed tickets ahead on busy weekends. If you've got teenagers who claim they're bored in Connecticut, this fixes it.

Get outside: the river, the trail, and the bridge

Portland Riverfront Park (284 Brownstone Avenue) is the easy one, a scenic stretch of green on the Connecticut River waterfront with a boat launch and room to walk. It's where you go for twenty quiet minutes by the water.

The Air Line State Park Trail runs right through Portland, a flat, crushed-stone rail-trail built on an old railbed. It's the move for an easy bike ride, a run, or a dog walk, and it connects Portland eastward toward East Hampton and beyond. No hills, no traffic.

And don't skip the Arrigoni Bridge itself. The 1938 double steel arch is the town's signature structure, and at the time it opened it was the most expensive bridge ever built in Connecticut at $3.5 million. There's a pedestrian walkway on each side, so you can walk out over the Connecticut River for the best free scenic view in town, downtown Middletown on one bank, downtown Portland on the other.

The brownstone history (and the spa coming to the quarry)

Portland's brownstone is the whole origin story. From the 1700s into the early 1900s, the town of Portland's quarries shipped that distinctive reddish-brown sandstone down the river and out to build the rowhouses of Brooklyn, Manhattan, and Boston's Back Bay. The quarrying stopped after the 1936 flood drowned the pits, and those flooded pits are exactly what Brownstone Adventure Park sits in now.

One thing to know: the old Quarry View Historic Park (311 Brownstone Avenue) is closed. A Canadian hospitality company is building a $50 million adults-only Nordic spa on the 6.3-acre quarry site, with cold-plunge pools, saunas, a waterfall, and a bistro. It's still under construction, so it's a "watch this space," not a visit-now. The history is the draw for the moment.

Where to eat and drink in Portland

Portland holds its own on food and drink for a town this size. Concentric Brewing Company (91 Main Street) is Portland's first brewery, with a real taproom, a beer garden, and an on-site kitchen (Graze) so you can make an afternoon of it. Arrigoni Winery & Cider Co. (1287 Portland-Cobalt Road, Route 66) is the rural family farm option, making its own cider and wine with local craft beer on tap. Gotta's Farm and Cider Mill (661 Glastonbury Turnpike, Route 17) is the seasonal farm stand everyone drives out for, open spring through fall with a pick-your-own orchard, a farm market, and cider donuts worth the trip.

For a sit-down meal, Sarah's On Main (246 Main Street) is the beloved breakfast and lunch spot, The Portland Ale House (188 Main Street) does pub food with 16 rotating taps and a serious burger, and Terrazza at Quarry Ridge Golf Course (9 Rose Hill Road) serves year-round Italian with a view over the fairways. The golf course itself is open to the public if you bring your clubs.

Common questions about Portland, CT

Is Portland, CT worth visiting? Yes, especially in summer. Brownstone Adventure Park alone pulls people in from across the state, and the riverfront, the Air Line Trail, and the brewery-and-cider pair make a full day. It's five minutes from downtown Middletown over the Arrigoni Bridge.

What is Portland, Connecticut known for? Its brownstone quarries. Portland sandstone built a huge share of the 19th-century brownstones in New York and Boston. The flooded quarries are now home to Brownstone Adventure Park and a Nordic spa under construction.

How do you get to Portland, CT? Cross the Arrigoni Bridge (Route 66/17) from Middletown, or take Route 9 to Route 17. It's in Middlesex County, on the east bank of the Connecticut River.

Is there a brewery in Portland, CT? Yes, Concentric Brewing on Main Street, plus Arrigoni Winery & Cider just out of town. Both are in our breweries near Middletown guide.

While you're across the river, here are the local guides to breweries near Middletown, free things to do in Greater Middletown, things to do with kids, and a perfect weekend itinerary. See what's on this week on our events page, browse past issues, or subscribe above for the Thursday rundown.