This New Haven County town is located on the banks of two important rivers, the Housatonic and Naugatuck.
Along the Ansonia-Derby-Shelton Highway on the Naugatuck River, Seymour has a small but vibrant downtown with independent shops and retro movie theaters showing classic movies.
Seymour has a long-established community of inspiring events, and the town pulls together under the Seymour Pink banner to raise funds and raise awareness for breast cancer.
In Seymour Country and neighboring towns, you can hike in state parks, play golf, and learn about Connecticut’s past at historic museums.
1. Downtown Seymour
Two or three blocks back on Main Street, the freeway doesn’t spoil the sweet little mess of local businesses.
Tickled Pink (23 Bank Street) is famous for its lovely handmade gifts, with more gift shops, coffee shops, tea rooms, yoga studios, art studios, musical instrument shops and more all within seconds of walking There are many shops.
If you’re hungry, a retro Tony’s Diner adds to the feeling that you might be in a time warp, or you can grab a New Haven-style pizza (First Street Apizza) down 1st Street.
2. Seymour Historical Society
The Local Historical Society is located at the Catherine Matisse House at 59 West Street.
This elegant home was built in 1940 by Katharine Matthies, the daughter of Seymour industrialist George Matthies.
Catherine died in 1987, and the Society, which took up residence in the 1990s, continues to help preserve the town’s history through a growing inventory of historic artifacts.
The Society is known for its special programs and events, and when we wrote this list, there was a compelling exhibit/display on the role of taverns in colonial New England society.
3. The Strand Theatre
A cornerstone of Seymour Street, the Strand Theatre is beautiful inside and out, with an original marquee and an auditorium with a stage and red velvet curtains.
Like the rest of Main Street, this movie theater looks like a time traveler from the 1950s and has been open since the Great Depression era.
Run by the local Knights of Columbus, the venue plays both cult classics and themed dual functions (think Rocky Horror Picture Show and John Carpenter movies). Keep an eye on the Facebook page as there’s also plenty of live comedy on the calendar.
4. Southford Falls State Park
Eight Mile Creek pours down a rocky landscape on its route from Lake Quassapaug to the Housatonic River.
These fast-flowing waters were once developed for industry at the Southford Falls State Park site on the Oxford-Southbury line, driving sawmills, mills and metalworking shops.
The Diamond Match Company set up shop here in the early 1900s, but handed over the site to the state in 1927 after two consecutive fires.
Visit to stroll by the creek, admire the scenic waterfall at the southeastern end, and cross a real covered bridge.
This is also a designated trout park and is often stocked for young and inexperienced anglers.
5. Dashan Cemetery
In the remote countryside near Holbrook Road, Big Mountain Cemetery has a rather moody setting, on a low hillside lined by deciduous forest.
It has been a cemetery since 1783 and is still in use today.
The cemetery can be visited during the day, where history and verdant scenery come together.
It can be fascinating to read some of the older inscriptions, many written for Revolutionary and Civil War veterans, and appreciate the skill of the engravers more than 200 years ago.
The oldest marker is an Abigail Fairy Child (d.1783), one of 21 graves from the 18th century.
6. Whitlock’s library
Also located in a peaceful rural area near Bethany, Whitlock’s Book Barn has been in business since 1948 and specializes in second-hand and rare books, old maps and mayflies.
It’s all housed in two rustic barns, fully stacked from floor to ceiling, a reading lover’s research dream.
Despite the remote feel of Whitlock’s Book Barn, New Haven and Yale Universities are only a few minutes’ drive away, so the bookstore is often flocked to by scholars for an intellectual journey.
7. Olde Sawmill Snack Bar and Micro Golf
A family treat in spring and summer, this attraction is located in a valley in Oxford Creek and is surrounded by deep mixed woodland.
You’ll find an imaginatively designed 18-hole miniature golf course set against the stream, embroidered with manicured shrubs and perennials.
If you can make a hole-in-one on the last hole, you win a free round.
The Olde Sawmill Snackbar has a deck overlooking the course and cooks hungry treats like burgers, hot dogs, sandwiches, wraps and fried seafood.
8. Osbornedale State Park
Successful businesswoman Frances Osborne Kellogg (1876-1956) pieced the land together through a series of shrewd investments in the early 20th century before bequeathing it to the nation in 1956 . On 417 acres of rolling hills and meadows that were once farmland, Osbornedale State Park is set on 6 color-coded walking trails that disappear into lush woodland past some impressive glacial boulders.
Pickett’s Pond on the southeast corner is a destination for anglers, with two gazebos and picnic tables on the shore.
On the south side of the park is the Osborne-Kellogg residence, and ice skating on Pickett’s Pond under the lights in winter.
9. Osborne Homestead Museum
Francis Osborne (later Osborne Kellogg) inherited the family estate in 1907 at the age of 31 and made the then brave decision to take on her father’s business responsibilities.
Over the next few decades, she built a small empire in the Lower Naugatuck Valley, but was also an ardent environmentalist.
You can walk into her beautiful Colonial Revival home, which dates back to the 1840s but was redesigned by Osborne in the 1920s.
On this tour, you’ll learn about the origins of the Osborne family and learn about Frances’ lasting impact on local industry, agriculture, the environment, and the arts.
The house is open from May to October, Thursday to Sunday, while the formal grounds, featuring a rose garden, trimmed shrubs and flowering trees, can be visited year-round and colorful in spring and summer.
10. Kellogg’s Environmental Center
Named after Francis’ husband, architect Waldo Stewart Kellogg, this nature-oriented attraction is busy with exhibitions, seminars, lectures and outdoor events throughout the year.
The Kellogg Environmental Center is also an important resource for teachers and students for educator workshops and inquiry-based field studies on environmental topics.
But for the general public, it’s a wonderful window into the natural world.
There are fascinating seasonal activities here, such as bird walks during migrations, a night dedicated to identifying moths, and presentations by experts like a CT State archaeologist who saw some spooky things in his day.
11. Savino Vineyards
This century-old, eight-acre vineyard near Woodbridge began production in 2006. Savino Vineyards grows American hybrid grapes and premium grapes such as Merlot, Pinot Noir, Cabernet Franc and white wines for the production of single-varietal wines and blends.
The tasting room is open weekends from the first weekend in May through the weekend before Thanksgiving.
One session costs $10 and includes a souvenir glass.
You can pair your wine with an appetizer platter, including cheese, olives, bread, salami and olive oil from the manufacturer’s own grove of Tegiano in Campania.
12. Naugatuck State Forest
The Naugatuck State Forest is made up of five blocks and spans 4,153 acres of wilderness in the Naugatuck Valley.
In downtown Seymour, you are just a few miles from the northern car park at the Quillinan Reservoir Block (on Rimmon Road).
There, you can take a purple multi-use trail that winds up and down the hills around some huge boulders and small rocky creeks.
To the north of Seymour are the West and East Sides, which have more dramatic rock formations, streams and mixed woodlands.
The West End has four reservoirs, two waterfalls and the stunning Spruce Creek Canyon with small waterfalls.
13. Woodhaven Country Club
Hidden in the woods of 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 run by their son Paul.
The course has a truly family vibe, and despite the accolades from the likes of Golf Digest, it remains off the beaten track.
The par 36 course is fun to play, with interesting layouts and tough pin positions on relatively loose greens.
The lush Bethany woodlands presented its own challenges, with the only open areas being on the water, which was subtly incorporated into the design.
Prices are so low that you can play nine holes on a weekday for just $21.
14. Bad Son Brewing Company
After a few stops on the New Haven Line or 10 minutes down the highway, you’ll reach Derby, home to a small craft brewery housed in a historic brick industrial building.
“BAD SONS” is an acronym for the Lower Naugatuck Valley Communities: (Beacon Falls, Ansonia, Derby, Seymour, Oxford, Naugatuck and Shelton) and features an outdoor patio, board games, foosball, shuffleboard A hop-up bar Sunday with balls and live music.
For food, the Dew Drop Inn (casual American) and Roseland Pizza deliver on Wednesdays and Thursdays, with revolving food trucks at other times.
As for beer, there are 11 beers available to drink in September 2019, including 5 hoppy IPAs, 2 sours, 1 red, 1 dark, 1 pale and 1 pale.
Prominent among them is Straight Six, a single-hop IPA brewed by Motueka with lime notes and a backdrop of lemon zest and tropical fruits.
15. Annual Events
Seymour has a cohesive spirit that shines through events throughout the year.
According to our count, there are seven big ones, the most unique of which is Smoke in the Valley (attended by BAD SONS), a craft beer festival in early October with mixed beers, great food and lots of live music.
The Christmas parade in early December runs from the community center through downtown Seymour with up to 50 floats.
Meanwhile, Seymour Pink, a nonprofit based in the town, fights breast cancer with programs such as pink recycling bins (instead of the usual blue) and walks, celebrations and festivals every season .
Where to Stay: Best Hotels in Seymour, CT (CT)
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