Looking for something fun to do this weekend in Southern CT? We’ve comprised a list of our personal favorites as well as those of area residents to showcase the local flavor of this unique New England town. From food to shopping and overnight accommodations, there’s no shortage of great stops on this list to give you a great day trip or getaway weekend this spring.
F O O D & D R I N K
Located inside the beautiful Heritage Hotel in Southbury is this great bar and restaurant. Perfect of dinner or drinks in a lively atmosphere with juke box and pool table available.
In room dining service for overnight guests as well as breakfast and lunch available.
522 Heritage Road, Southbury CT
Three generations later, Denmo’s in Southbury is still one of the most poppin’ places in town. Great for a quick bite, this is the ultimate food stop for a sunny afternoon where patrons can sit outside at one of the many picnic tables or tailgate on the back of a car. No interior dining available, this is a food window style experience. Chili dogs, Hotdogs and Clamstrips just some of infamous offerings here. Check it out for yourself! It’s a great bike stop too! | Website | 203-264-4626 | IG: @denmosfamousoriginal
9am – 10 pm daily.
340 Main Street South in Southbury, CT
Leo’s is located in the heart of Southbury in the plaza of Adorn Restoration Boutique. In operation since 1987 Leo’s offers a variety of breakfast, lunch & dinner menu items in a traditional American style. Interior is a diner vibe, with friendly staff and plenty of comfortable seating. Website | (203) 264-9190 | IG: @leos_restaurant
The Olive Tree is located in a refurbished house on the Southbury/Woodbury town line. A full service service dining room is surrounded by windows and overlooks a large outdoor patio. Parties of all sizes welcomed. Since 1980 owner and chef has served a mix of culturally inspired dishes. Warm atmosphere, cozy dining. Closed Sunday & Monday.
Website | (203) 263-4555
1204 Main Street South. Woodbury / Southbury line
Locally loved pizza restaurant, authentic Italian fare, casual dining, located steps from I-84 and across the street from Maggie Mcflys.
1056 Main St S, Southbury, CT 06488
This charming restaurant is located on the elite Heritage Village golf course. The menu includes pub dishes, pastas, seafood, steaks, salads and specials. The dining room over looks the rolling green and the bar features a cozy atmosphere with an additional patio and dining space to accommodate private parties.
137 East Hill Rd, Southbury, Ct, 06488 – (e): JJcountrytavern@yahoo.com
S W E E T S
Homemade Ice Cream, Cakes & Sweet Treats. Multiple Locations.
385 Main Street South Southbury,CT
S T A Y
Located in the heart of Southbury in the Heritage Village, the hotel features two salt water swimming pools, suites overlooking the golf course with jetted tubs, a full service tavern and bar, multiple game rooms and gathering areas, beautiful fireplaces throughout, a luxury day spa as well as a new winery, a golf course, multiple event venues, tennis courts and more, just steps from retail shops in the village.
2018 The Heritage Hotel Golf, Spa & Conference Center 522 Heritage Road, Southbury, CT 06488
This historic home, built in 1818, by John Moseley captures quintessential New England charm with modern amenities. It’s route 6, Southbury location provides easy access to all the destinations listed in this guide, & more! Beautiful grounds in a peaceful country setting. “Enjoying a cup of coffee on the stone patio or taking a book by the fireplace. Our grounds are the perfect backdrop for any event including reunions, engagement parties and intimate wedding ceremonies and receptions.” – Innkeeper
782 Main Street North, Southbury, CT 06488
S H O P
Adorn Restoration Boutique is a group shop featuring multiple dealers, custom furniture, antiques and repurposed designs as well as vintage wears, clothing, jewelry and home goods.
7 Poverty Road, Bennet Square, Southbury
VINTAGE TREASURES LLC.
Unique vintage home goods, multi-dealer antique shop, artisan wares, vintage, antique & contemporary consignments.
Pasta lovers rejoice! This artisanal pasta shop offers handmade pastas, sauces as well as specialty goods both local and from Italy. Fresh filled cannoli’s & Bridgewater Chocolates available. The best homemade ravioli.
O T H E R – L O C A L – F A V O R I T E S
MAISON ST. GERMAIN
Specialty antique & vintage home furnishings shop located behind Carol Peck’s Goodnew’s Cafe. Home Decor, Rustic Treasures & Refinished Furniture.
website | 203 266-4223
Connecticut’s oldest continually operational Inn & Tavern, unique ambient dining experience upstairs, downstairs bar and more casual pub. Delicious classic American fare. Visit website for more info and overnight accommodations and suggested call for dinner reservations: (203) 263-2101
Craft Brewery in the heart of Woodbury. Tap room tastings, Full bar, Pub Fare, Live Events.
KETTLETOWN STATE PARK, SOUTHBURY CT
Kettletown State Park public recreation area is located on the eastern shore of the Housatonic River’s Lake Zoar. Seasonal activities include hiking, swimming, camping, picnicking, and fishing.
1400 Georges Hill Rd, Southbury, CT 06488
S H O U T O U T S
C O N T A C T U S
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This guide was sponsored by the Heritage Hotel