15 Best Things to Do in Seymour (CT)

This little town in New Haven County is on the banks of two important rivers, the Housatonic and the Naugatuck.

Tracked by the Naugatuck River’s Ansonia-Derby-Shelton Expressway, Seymour has a small but animated downtown, with independent shops and a retro cinema playing classic movies.

There’s a historical society in Seymour putting on edifying events, and the town pulls together for various activities under the Seymour Pink banner, raising funds and awareness for breast cancer.

Out in rural Seymour and the neighboring towns you can hike in state parks, play golf and dip into Connecticut‘s past at historic house museums.

1. Downtown Seymour

The expressway does nothing to spoil the sweet little jumble of local businesses in the space of two or three blocks behind Main Street.

Tickled Pink (23 Bank Street) is known far and wide for its cute handmade gifts, and within seconds on foot there are more gift shops, a coffee shop, a tearoom, a yoga studio, art studios, a musical instrument shop and a whole raft of antiques stores.

If you get peckish, the retro Tony’s Diner adds to the feeling you might be in a time warp, or you could go down 1st Street for New Haven-style pizza (First Street Apizza).

2. Seymour Historical Society

The local historical society is in the Katharine Matthies House at 59 West Street.

The elegant home was constructed in 1940, and Katharine Matthies was the daughter of the Seymour industrialist George Matthies.

Katharine passed away in 1987 and the society took up residence in the 1990s, continuing to help preserve the town’s history with an ever-growing inventory of historical artifacts.

The society is known for its special programs and events, and when we wrote this list there was a compelling exhibition/presentation about the role of taverns in Colonial society in New England.

3. Strand Theater

A cornerstone of Seymour’s Main Street, the Strand Theater is a thing of beauty inside and out, with an original marquee and an auditorium with a stage and red velvet curtain.

Like other parts of Main Street, this movie theater looks like a time traveller from the 1950s and has been open since the Depression Era.

The venue is operated by the local Knights of Columbus and plays cult classics, and themed double features (think Rocky Horror Picture Show and John Carpenter movies). Keep close tabs on the facebook page as there’s also plenty of live comedy on the calendar.

4. Southford Falls State Park

On its course from Lake Quassapaug to the Housatonic River, Eight Mile Brook cascades through a rocky landscape.

These fast-moving waters were once exploited for industry at the site of Southford Falls State Park, on the Oxford-Southbury line, driving sawmills, gristmills and metalworking shops.

In the early 20th century the Diamond Match Company set up shop here, but handed the site over to the state in 1927 following two successive fires.

Pay a visit to stroll next to the brook, admire the scenic falls at the south-east end and cross a genuine covered bridge.

This is also a designated trout park, frequently stocked for younger and less experienced anglers.

5. Great Hill Cemetery

In remote countryside off Holbrook Road, Great Hill Cemetery has a rather moody setting, on a low hillside cloaked by deciduous woods.

This has been a burial ground since 1783 and is still used today.

The cemetery can be visited during daylight hours, for a mix of history and verdant scenery.

It can be fascinating to read some of the older inscriptions, many for Revolutionary and Civil War veterans, and admire the skill of carvers more than 200 years ago.

The oldest marker is for one Abigail Fairchild (d.1783), one of 21 graves from the 18th century.

6. Whitlock’s Book Barn

Also in a peaceful rural spot in nearby Bethany, Whitlock’s Book Barn has been open since 1948 and specializes in used and rare books, old maps and ephemera.

This is all housed in two rustic barns, which are completely stacked from floor to ceiling, and a dream for book lovers to investigate.

Despite Whitlock’s Book Barn’s remote feel, New Haven and Yale University are minutes away by car, so the store is often flocked by academics on a intellectual odyssey.

7. Olde Sawmill Snackbar and Miniature Golf Course

A family treat in spring and summer, this attraction is in a hollow on the Little River in Oxford, fringed by deep mixed woodland.

What you’ll find is an imaginatively designed 18-hole miniature golf course, mingling with the stream and embroidered with trimmed shrubs and perennials.

If you can get a hole in one on the final hole you’ll win a free round.

The Olde Sawmill Snackbar has a deck overlooking the course and cooks up hunger-stomping fare like burgers, hot dogs, sandwiches, wraps and fried seafood.

8. Osbornedale State Park

The successful businesswoman Frances Osborne Kellogg (1876-1956) pieced together this land through a series of shrewd investments in the early 20th century before bequeathing it to the state in 1956. In 417 acres of rolling hills and meadows, on what used to be farmland, Osbornedale State Park can be discovered on six colour-coded walking trails, disappearing into lush woodland and past some impressive glacial boulders.

Pickett’s Pond in the southeast corner is a destination for anglers, and has two pavilions and picnic tables on its shores.

In the south of the park is the Osborne-Kellogg residence, and in winter there’s ice-skating on Pickett’s Pond under lights.

9. Osborne Homestead Museum

Frances Osborne (later Osborne Kellogg) inherited the family property in 1907 at the age of 31, and took what was then a brave decision to assume her father’s business responsibilities.

Over the next few decades she built up a small empire in the Lower Naugatuck Valley, but was also a keen conservationist.

You can step inside her beautiful Colonial Revival home, dating back to the 1840s but reworked by Osborne in the 1920s.

On a tour you’ll get to know the roots of the Osborne family and learn about Frances’ lasting impact on local industry, agriculture, the environment and the arts.

The house is open May to October, Thursday to Sunday, while the formal grounds, with rose garden, clipped shrubs and flowering trees, can be visited year round and are at their colourful best in spring and summer.

10. Kellogg Environmental Center

Named for Frances’ husband, architect Waldo Stewart Kellogg, this nature-oriented attraction has a busy program of exhibitions, workshops, talks and outdoor activities throughout the year.

The Kellogg Environmental Center is also a key resource for teachers and students for its educator workshops on environmental topics, and inquiry-based field studies.

But for the general public it’s a wonderful window on the natural world.

There are engaging seasonal activities here, like bird walks during migration periods, a whole night dedicated to identifying moths and presentations by experts like the CT State Archaeologist, who has seen some spooky things in his time.

11. Savino Vineyards

Vineyards and Wineries — Vineyards And Wineries

Around a century-old barn, this vineyard close by in Woodbridge is in eight bucolic acres and started producing in 2006. Savino Vineyards cultivates American hybrid grapes and premium vitis vinifera like Merlot, Pinot Noir, Cabernet Franc and Seyval Blanc, for single varietal wines and blends.

The tasting room is open on weekends from the first weekend in May to the weekend before Thanksgiving.

A session costs $10, with a keepsake glass included in the price.

You can pair your wine with an antipasto platter, including cheeses, olives, bread, salami and olive oil from the maker’s own grove in Teggiano, Campania.

12. Naugatuck State Forest

The Naugatuck State Forest is composed of five blocks across a total 4,153 acres of wilderness in the Naugatuck Valley.

In downtown Seymour you’re just a couple of miles from the northern parking lot (on Rimmon Road) for the Quillinan Reservoir Block.

There you can get onto a purple-blazed multiuse trail wending its way up and down hills, around some massive boulders and over little rocky brooks.

Just outside Seymour to the north are the West and East Blocks, for more dramatic rock formations, streams and mixed woodland.

In the West Block are four reservoirs, two waterfalls and the stunning Spruce Brook Gorge, which is bedded with cascades.

13. Woodhaven Country Club

Tucked in the woods in Bethany is a highly-rated nine-hole public golf course.

Woodhaven Country Club was founded in the 1960s by Ben and Ag Falcone, and is now being run by their son Paul.

There’s a real family atmosphere at this course, which, despite acclaim from the likes of Golf Digest, remains off the beaten track.

The par 36 course is a joy to play, with a fun layout and tough pin positions on relatively forgiving greens.

The dense Bethany woodland poses its own challenge, and the only open areas are on water, which is smartly integrated into the design.

Rates are remarkably low, and you can play nine holes on a weekday for just $21.

14. BAD SONS Beer Co.

A couple of stops on the New Haven Line or ten minutes down the expressway and you’ll be in Derby, where there’s a great little craft brewery in a historic brick industrial building.

“BAD SONS” is an acronym of lower Naugatuck Valley communities: (Beacon Falls, Ansonia, Derby, Seymour, Oxford, Naugatuck and Shelton), and has a hopping taproom with an outdoor yard, board games, foosball, shuffleboard and live music on Sundays.

Food-wise, Dew Drop Inn (American casual) and Roseland Pizza deliver on Wednesdays and Thursdays, and there are rotating food trucks at all other times.

As for beer, there were 11 on tap in September 2019, counting five hoppy IPAs, two sours, a red ale, a stout, a lager and a pale ale.

A standout was Straight Six, a single-hop IPA brewed with Motueka and with a lime palate and background of lemon zest and tropical fruit.

15. Annual Events

Seymour has a tight-knit spirit that shines through at events throughout the year.

There are seven big ones by our count, and one of the most unique is Smoke in the Valley (attended by BAD SONS), a craft beer festival in early-October, mixing brews, great food and lots of live music.

The Christmas Parade at the start of December works its way through downtown Seymour from the Community Center and has up to 50 floats.

Seymour Pink meanwhile is a non-profit based in the town and fighting against breast cancer with all sorts of schemes like pink recycling bins (instead of the usual blue) and walks, galas and festivals in every season.