A Romantic Weekend Getaway to Connecticut

Last weekend was my 18th wedding anniversary. We were invited by Heritage Hotel in Southbury, Connecticut to spend our special weekend there and explore the surrounding area. The southwestern portion on the state is the perfect spot for a romantic getaway in Ct. Between the property itself, the lush verdant landscape and the food and beauty of the farms, we had a fabulous time. Here are a few of the things we did on our romantic weekend and a few more ideas, so that you can plan your own weekend getaway to Connecticut. Everything we did was within an hour drive from our home base of Southbury.

best romantic getaways in new england
Me and my honey celebrating our 18th anniversary with some wine tasting and exploring. He doesn’t actually drink, but is still is happy to explore the wineries with me.

Hiking Trails in western Connecticut

Getting into nature is always one of our favorite ways to relax and bond. The area is full of lush trees, in a particularly stunning dark green color. Here are a few great trails in Ct.

Audubon Center at Bent of the River

Audubon Centers are always lovely places to hike. This one has 15 miles of trails with small waterfalls and views. Some of the trails were damaged in recent storms, so be sure to check with them before planning your hike.

Lover’s Leap State Park in New Milford

Lover’s Leap legends abound and hikes to them promise a great view. You can check out another one we take at Purgatory Chasm in Massachusetts. This park also contains the Berlin Iron Bridge one of only five remaining iron bridges in Connecticut. The moderately easy hike to Lover’s Leap crosses the Housatonic River over that bridge and is 1.1 miles long.

Kent Falls State Park

Ct waterfall hikes
The lower falls at Kent Falls State Park. There are lookouts all along the trail to see more of the waterfall’s cascades.

If you are looking for a fairly easy (but a bit steep) hiking trail in Ct with waterfalls, this place is perfect! Not only is there one waterfall, there are many cascading falls as you ascend this quarter mile well-marked and maintained hike. Dogs are allowed on a leash and there are many spots for a romantic picnic in the large park at the foot of the falls. I am a huge fan of impressionism and this park has an informative exposition about American Impressionism.

Covered Bridges in Connecticut

You have to admit, covered bridges are about as New England romantic as you can get. There is one that you walk over on the trail to Kent Falls or you can stop by the larger and more historic Bull’s Bridge in South Kent on your way. Also check out the West Cornwall Covered Bridge.

Ct Antiques Trail

Things to do in Connecticut for the weekend
Monique Shay Antiques in Woodbury, Ct.

Wandering around the winding roads in western Connecticut stirs longing for Americana. Take some of that feeling home with you by buying a piece of it in any of the antiques stores along Connecticut’s Antiques Trail.

Enjoy the harvest of the land.

Sample along Connecticut’s Wine Trail.

Like I said, this area is so green– so you can imagine the yumminess that grows here! We spent one afternoon stopping in at a few local wineries. Most of them offer tours and tastings for a small fee. They are a wonderful spot to stop for a picnic. Many have farm-to-table meals. Here are a few of the nearby wineries–

White Silo Farm, Sherman, Ct

My taste in wines tend toward sweet, so I was instantly drawn to this winery. It used to be a fruit farm until the owner decided to start using his fruit to make wines. Not only with fruits I expected, like blackberry and raspberry, but also rhubarb. Surprisingly they aren’t all sweet, but they were very good. They also carry house-made pastries that are inventive and incredible. Their website is a little unclear about the timing of tours- they are only offered once a day, 1 pm on the day I arrived.

Walker Road Vineyards, Woodbury, Ct

The vineyard has tastings Saturdays and Sundays 12-5, May through December. This is a small winery where you can picnic and meet the owner in his 150-year-old barn.

DiGrazia Vineyards, Brookfield, Ct

This family-owned vineyard welcomes picnickers and is moving towards being organic-certified.

Hawk Ridge Farm, Watertown, Ct

Set on a larger horse and hay farm, visiting is a great way to get an farm experience while you are tasting.

Heritage Hotel, Southbury, Ct

Right by the tennis court in the hotel are newly planted vines. This would be an incredibly romantic place for a wedding or vow renewal. In about three years, they will start pressing the grapes to begin making wine.

Eat Some freshly-made ice cream.

Weekend Getaways in Ct
The candy-colored sunset matches the multitude flavors of ice cream at Rich Farm, Ct. My cookie dough ice cream was blue.

Rich Farm, Oxford, Ct

So fresh, we ate it with the cows. But seriously, this ice cream is deliciously creamy and the cows are so cute. It is set on a hill, so a perfect spot to take in the sunset.


I do tend to have a hard time sitting still, but somethings are easy to stop for…

Start your day with breakfast in bed.

romantic getaways in Connecticut.
Salmon and pancakes for breakfast… without leaving the comfort of our room!

To get ready for our day of adventure, we started it with a leisurely breakfast in bed.

The Spa at the Heritage Hotel

I had a dreamy massage with a floral exfoliation while my husband had a Swedish massage. The jasmine scent I chose was divine and Heidi gave one of the best massages I have ever had. You should definitely make time for a visit. Explore the spa menu.

weekend getaway to Connecticut
Heritage Hotel has both indoor and outdoor pools to relax by.

Take a yoga class.

Included in all stays at Heritage Hotel is entrance into their fitness club, including their tennis courts and fitness classes. We love to do yoga together.

Take a soak in the hot tub or a steam in the sauna at the Heritage Hotel.

No better way to end a day than by seeing a sunset, then relaxing in a sauna or hot tub.

Hotels in Southbury, Ct.
Our spacious room at Heritage Hotel in Southbury, Ct.

The staff at The Heritage Hotel, Spa and Conference Center was so friendly and made our weekend fabulous. Visit their website to book a room for yourself and have a fabulous romantic weekend getaway in Connecticut.

Read on for more Connecticut and New England posts or explore my US Road Trip Guide. New York is right next door too!

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16 thoughts on “A Romantic Weekend Getaway to Connecticut”

  1. Seems you guys had a great time there! Heritage Hotel looks so cute and peaceful. And their breakfast in bed got me, haha 😀

  2. Amazing way to celebrate an anniversary! May all the happiness be with you at all times! This weekend getaway in Connecticut seems a great option to combine outdoors with relax!


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