Summer Getaway: 48 Hours in Ridgefield, CT

Summer day on Main Street in Ridgefield, CT

If you’re seeking a peaceful yet lively getaway to one of Connecticut’s most charming towns, you’ve come to the right place. Ridgefield is home to rich history, fantastic food, a buzzing arts and culture scene, and picturesque scenery all wrapped up in a quaint New England town. Join us as we take you through the perfect summer weekend getaway in Ridgefield!

Check In in order to Check Out

If you’re traveling from out of town, arrive to town early if you can and get the lay of the land – you’ll love enjoying a summer afternoon on Main Street. Grab an afternoon pick-me-up on Main Street at Tazza Café, Queen B Coffee Company, or Botanika Café while waiting to check in to the charming West Lane Inn or Fountain Inn down the road. (If you’re gluten free or health-conscious, you’ll especially love Botanika!)

After checking in (or “checking out” of the home routine), get settled in your room and perhaps enjoy a moment of welcome solitude on the porch before dinner. Grab a glass of wine or lemonade, a book, or just shut your eyes and bask in the blissful peace of summer.

Staycationing? This fun itinerary can easily be applied to locals looking for a quick summer escape as well. Take a break from the routine and enjoy these tempting offerings in your own backyard.

The Fountain Inn
West Lane Inn

Dine Out

With so many options for dinner it might be hard to decide where to go! No matter whether you feel like hopping in the car or strolling down Main Street, Ridgefield’s restaurant selection will leave you planning your next meal before you’ve had the first.

Whether you’re a 10-second or 3-minute walk away, Ridgefield’s newest spot, The Benjamin, will delight your palate with its French-American menu. Enjoy a walk into town down Main Street where you’ll find a plethora of wonderful dining options. The new Brasserie Saint Germaine focuses on classic French fare, while Bailey’s Backyard will wow you with seasonal and local farm-to-table flavors.

Dessert at The Benjamin
Bailey's Backyard

Check out Tequila Escape for Mexican food and killer cocktails that are far from average, and Tablao Wine Bar & Restaurant for Spanish cuisine and a great wine list. Tucked behind Main Street near Tablao is 850 Degrees, where you’ll experience authentic Italian cuisine and delicious pizza.

While many restaurants in Ridgefield offer outdoor seating, you may prefer to really make the most of a summer evening outside. Take out a picnic-friendly meal or a selection of tapas and enjoy a CHIRP Concert at beautiful Ballard Park right downtown! Our Events Calendar will keep you abreast of everything happening in Ridgefield, so be sure to check it out while you make plans.

Tequila Escape @tequilaescape
Tablao Ridgefield

If dessert menus aren’t your style or you need a moment to digest after, grab an ice cream cone from Deborah Ann’s Sweet Shoppe or Gofer Ice Cream downtown. Enjoy a casual stroll along Main Street or sit on the patio outside Deborah Ann’s and watch the world go by. No matter what you choose, your walk back to your inn will help burn some of those calories!

Rise & Shine

Rise and shine for a great homemade breakfast at the inn accompanied by a perfectly brewed cup of coffee or tea. Or head out for fresh baked goods from Ross Bread or a hearty diner breakfast at Dimitri’s or Wooster Hollow Café.

After your morning energy intake, hike or ride through one of Ridgefield’s many parks and trails. With stunning vistas and trails for all activity levels, spending time in nature is the perfect way to start a beautiful day.

Walk up through Jones Trail and take a peek at The Hickories’ property, a beautiful farm north of town, and a beautiful drive up to boot. Take a pre-lunch dip at Martin Beach Park and cool off. And the new Ridgefield Farmer’s Market will take place every other Saturday on the original town green, so be sure to check our Events Calendar to see if it’s happening during your stay.

Bennett's Pond State Park @graysonhughofficial
Martin Beach Park @fitnessbysami

Afternoon on the Town

After all that hiking, it might already be time for a little lunch and some shopping! Enjoy a casual outdoor lunch at Southwest Café or Bareburger. Both just north of downtown, you’ll be treated to a lunch that will recharge you for the rest of the day. For a slice of pizza and a salad, pop by 850 Degrees, or for a traditional barbecue menu, deck seating and a great view, take a ride up to Odeen’s at the Ridgefield Golf Course.

Odeens BBQ Restaurant at Ridgefield Golf Course
Afternoon pick-me-up on Main Street at Botanika Café

Summertime Shopping

Ridgefield is full of fabulous local shops so whether you’re looking for a memento or something that didn’t make it into your suitcase, you’ll find just what you’re looking for, and maybe more!

Men and women alike will love J. McLaughlin’s selection of luxurious clothing – you just might find a special piece for your weekend getaway. Olley Court and Bella Home also offer select women’s pieces and they’ll dazzle you with their wide selection of beautiful home goods. Bella Home also offers Ridgefield-themed goods too including keychains, coasters, cocktail napkins and more.

Olley Court

Missing the perfect vacation read or just need a new story? Stop into Books on the Common, the local independent bookshop and purveyor of more than just books. If bling is your take-home memento of choice, stop into Addessi Jewelers or the Guilded Lynx Studio where you’ll find unique and even locally handmade pieces.

Arts & Culture Experiences

Spend an entertaining afternoon engaging in the arts scene! The Aldrich Museum of Contemporary Art showcases unique exhibits including occasional after hours events, and RPAC Gallery, D. Colabella Fine Art Gallery, and the Ridgefield Guild of Artists offer ever-changing exhibits featuring local, resident, and renowned artists.

Books on the Common
Gallery Opening at D.Colabella Fine Art Gallery

A summer afternoon is also a great time to explore Ridgefield’s robust history. Visit the Keeler Tavern Museum & History Center where tours and exhibits will immerse you in a simpler time while you learn about life in Ridgefield from the Revolution to early 20th century. You can also lace up your walking shoes and do as much or as little of the Museum in the Streets tour as you like! This unique two-mile discovery trail guides you through thirty locations of historical significance, encouraging both discovery and preservation of this quaint town.

A stroll down Main Street in Ridgefield
Keeler Tavern Museum

Is a rainy day preventing walking activities? The Prospector Theater is always prepared with a silver screen and a bucket of homemade gourmet popcorn! Or visit one of the museums in town to get inspired by arts and culture.

Ridgefield is full of breathtaking scenic drives, too. Ridgebury Road and Salem Road, in particular, will have you yearning (or grateful) for life in the Connecticut country. There is no bad way to go, though, so get lost in Ridgefield – you’ll love it.

The Prospector Theater
The Aldrich Museum

Make A Night of It

Get tickets for a show at the Ridgefield Playhouse or Ridgefield Theater Barn and make an evening of it! Enjoy the show with dinner before or after – you’ll be glad to choose from the many options you didn’t get to enjoy the night before. Perhaps start with a cocktail or glass of wine at Tablao Wine Bar & Restaurant or Tequila Escape and then stroll over to another spot to maximize your culinary experience.

Feeling super casual? Head up to Nod Hill Brewery for live music and laid back but yummy fare from the rotating schedule of food trucks. Whatever time you return home, remember to take it all in before you shut your eyes. Take a moment to sit on the porch, listen to the crickets, and take a few deep breaths of the fleeting summer air.

Ridgefield Theater Barn
Nod Hill Brewery

Enjoy A Long Goodbye

One full day goes quickly so be sure to take advantage of every single moment before reality beckons. Enjoy a final, slow breakfast at the inn and bask in the luxury of being served this first meal of the day – and not having to clean up! If you’re visiting post-summer, enjoy the Keeler Tavern Museum’s First Sundays or stop by the Peter Parley School House for a deeper dive into town’s history. Was there something you couldn’t squeeze in to just one full day in town? Now’s the time! Do a little shopping, strolling, walking, or exploring before lunch at your delightfully over-long list of dining options.

Keeler Tavern Museum
Window Shopping along Main Street

As sad as it can be to bid adieu to a weekend away, that’s also the gift of a few days well spent. We can’t wait for you to visit our charming slice of Connecticut and hope you’ll tag us when you’re here at @inridgefield.

Here’s to happy summer travels!

Ridgefield ChamberThank you to the Ridgefield Chamber of Commerce for supporting the Ridgefield community!