Day Trip to Newtown, Connecticut; Hikes, Waterfall, & Food!

A fun day trip in Connecticut, the Newtown area has it all! From a list of hikes to choose from, cafes, a chocolate shop I still think about today, and too many great restaurants to choose from.

Check out this itinerary for a hiking day trip to Newtown, Connecticut!

A lifelong resident of CT, I rarely venture to the southwestern part of the state to hike or visit. I guess I associate towns close to Fairfield County (or in this case in Fairfield County) as busy – too busy & for me to find the peace and quiet I seek when I venture out to hike.

But Newtown, and specifically its village of Sandy Hook, has that rural and quaint New England feel to it.

There are some towns where when I leave I can’t wait to be back home in the woodsy nook of our Avon condo. But I didn’t get that feeling in Newtown which is why it makes for a perfect and adventurous day trip in CT.

It could be because at 38,644 acres/60.38 square miles, Newtown is quite spread out and is the fifth largest town, area-wise, in the state.

Now let’s get to planning a fun visit to this area of CT!

Adventurous Day Trip Itinerary for Newtown, Connecticut

1st stop: Choose a morning hike 🥾🥾

You have several choices here and it can depend on which area of CT you’re coming from as these hikes surround the Newtown area. Check out the length, difficulty, time, and the photos to see which of these hikes you’d like to try.

🥾Rockhouse Hill Sanctuary Loop, 4.7 miles, moderate

As AllTrails correctly states, this 4.7-mile loop took us about 2 hours to complete. There is a little incline here and there (630 ft elevation gain total) but it’s spread out over the whole hike which makes it a little easier.

There’s an overlook here that would be amazing in summer or fall where you can see the Housatonic River below.

🥾Southford Falls Loop, 1.7 miles, easy

Enjoy an easy walk to see a waterfall at Southford Falls State Park!

You don’t even have to do the whole loop if you only want to see the waterfall since Southford Falls (and the covered bridge! ❤️) is to the right at the beginning of the trail.

If you go counterclockwise around the loop you’ll hit the waterfall first and then continue to walk along Eightmile Brook before it loops around.

🥾Zoar Trail, 6.3 miles, moderate

Located in Paugussett State Forest with 1,113 feet of elevation gain, this is a more challenging hike and takes about 3+ hours to complete. You’ll enjoy the water views as you hike along Lake Zoar looking across the water at Kettletown State Park and you’ll also see Prydden Brook Falls waterfall. Click here for a shorter option of this trail at just 3.6 miles.

🥾Lillinonah Upper Half Loop, 3.1 miles, moderate

Another favorite trail in the Paugussett State Forest. I love how this loop hugs the Housatonic River so you have views of the water as you hike. This trail takes under two hours to complete and if you are looking for a longer version check out the 5.9-mile Lilinonah Trail.

2nd: Lunch or Dinner & Snacks

After the hike you have a choice of where to go for food after.

🍫Must stop: Castle Hill Chocolate 🍫💝

Located in Sandy Hook, a village of Newtown, is this must-stop chocolate shop. Made with love and almost too beautiful to eat, I loved the truffles, the dark chocolate-covered Oreo (a must!), and their famous hot chocolate. You can even buy their hot chocolate mix to take home!

Late breakfast or lunch: Sandy Hook Cafe

Open 9 – 5 every day, stop here for a baked treat, breakfast omelet, salad, or sandwich. We just got a latte and a cookie after our hike but loved sitting out on their back patio which overlooks a wide running stream with small rapids and a pretty path running alongside it.

Dinner choices:

Foundry Kitchen & Tavern

Also located in Sandy Hook, I loved the Asian influence on the menu here. From the short rib dumplings to the Thai curry rice dish I got. We loved everything on the menu here, my only complaint was that I could’ve had a bigger dish!

Farmhouse Restaurant

If you’d like to eat in downtown Newtown, then check out the highly rated Farmhouse Restaurant. They specialize in seasonal menus designed with ingredients sourced from the farmlands, fields and oceans of the northeast. The readers of Connecticut’s Natural Nutmeg magazine voted Farmhouse as a top 10 favorite farm to table restaurant in Connecticut!

I hope you enjoyed this day trip itinerary to the area of Newtown, Connecticut.

Clearly, my days are shaped around hiking so if that’s you, too, then I’m sure you will enjoy your day with this list of Newtown area hikes and restaurants! And of course, the chocolate shop.

I will be back!!

Enjoy! 🥾❤️👏🍫