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100 Things to Do This Summer in Litchfield County
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100 Things to Do This Summer in Litchfield County

By Allie Steers, Harry Harwood, and Julia McMurray

Litchfield County has been a summer retreat for many for generations. The beautiful scenic views, numerous lakes and waterways, variety of restaurants, and strong art scene makes for a memorable summer. We’ve put together a list of 100 things to do this summer—whether you live or vacation in Litchfield County—here are some ways to make the most of your summer!

1. Paddle a six or ten mile section of the Housatonic River with Clarke Outdoors in West Cornwall. Open by appointment only.

2. Stop by the Woodbury Lions Club’s annual Car Show and Summerfest in Hollow Park on June 2nd from 9 AM- 3PM!

3. Hike the Roxbury Land Trust trails. There are over 32 preserves with 30 miles of hiking trails, historical landmarks, and quiet places to enjoy Roxbury’s scenery.

4. See all the waterfalls in Litchfield County. Do go chasing waterfalls.

5. Pop into Litchfield Distillery and take a short and interesting tour of their facility and sample their award-winning spirits. The tours and tastings are free. Booking in advance on is encouraged. Make sure to try their newest Agave selection and their summer vodkas—blueberry and strawberry.

6. Experience some of the most idyllic country roads in our area on bikes. Covered Bridge Electric Bike in Cornwall has a variety of e-bikes for rent and will fit you for your size and needs. If you go, be sure to check out the scenic route along the river to Falls Village. Book your custom or group E-Bike tour with area adventure leaders at KC&E!

Covered Bridge Electric Bike

7. Hike the trails at Steep Rock Preserve in Washington. There are trails for all ages and levels of experience. Find the historic Holiday House trail, go up the mountain to enjoy a beautiful vista, or hike through the old tunnel carved through rock for a long ago train route.

8. Grab a cup of coffee and a bite to eat in Washington after a hike at one of these charming cafes.

9. Get your fair fix at the Goshen Country Fair featuring games, amusement rides, contests, exhibitions, and fair food.

10. Enjoy outdoor dining. Our readers voted The White Horse in New Preston as best outdoor seating with Hopkins Inn and The Owl Wine and Food Bar in second and third place. Find a lively social scene with a beautiful view at West Shore Seafood in Morris; and in Sharon, head out for French at Le Gamin or try the darling wine bar The Edward. Also enjoy a delicious meal at The White Hart Inn in Salisbury.

11. Go for a hike along part of the Appalachian Trail which spans from Kent to Salisbury

12. The White Memorial Conservation Center in Litchfield has 40 miles of trails to explore, special events, and programs for all ages. The boardwalk hike is a must do.

13. Enjoy jazz music at the Litchfield Jazz Festival Opening Gala on June 13. The Gala runs from 5:45-7:00pm and the concerts start at 7:15 pm.

14. Tour the historical places in Torrington, including the John Brown birthplace site, Torrington Historical Society. Visit the newly developed walking area in downtown, the art galleries, and numerous restaurants including Geppetto Osteria e Bisteccheria  to check out their outdoor patio style seating and outstanding, authentic Italian food!

15. Visit the Eric Sloane Museum in Kent. View his paintings, illustrations, and collection of early American hand tools. While there, walk next store to the Connecticut Antique Machinery Association for a look at historical trains, tractors, a fully restored 19th century schoolhouse, and mining/mineral museum.

16. Relax and listen to live music at South Farms’ Summer Socials every Thursday night from 5-8 PM throughout June-September. There will be live music, food trucks, local beer, and more. Be sure to check out the new Boardwalk that was built at South Farms this summer! Walk over to Pasture Food Truck park for more food, cocktail options, and enjoy the growing flower fields and views on Thursday night Social nights.

17. Head to 100 Main Street in Falls Village curated by Bunny Williams and Christina van Hengel for one-of-a-kind products made by local artisans.

18. Feel like you are getting away to France at one of these French restaurants:

19. Spend the day shopping in the village of New Preston at these beautiful shops:

  • J. Seitz & Co. has home accents; womens, mens, and childrens clothing; apothecary; and gifts.
  • Plain Goods has collections for the home and wardrobe that are meant to be long lasting.
  • Privet House for everything you need for your home. From kitchenware, tableware, apothecary, and housekeeping.
  • DK Schulman for special gifts, stationary, baby items, and jewelry.
  • Pergola will be a sensual shopping experience for everything home and garden.
  • Frecha Design for modern Scandinavian furnishings, Argentine textiles, and distinctive works from local and international artists.

Afterwards get a drink and bite to eat at The Owl Wine and Food Bar.

20. Woodbury is home to some cute gift shops and antique shops.

  • Shop Cathy B has summer essentials for women; accessories; baby clothing, gifts, and accessories.
  • The Hidden Acorn offers vintage furniture, antiques, and restoration products.
  • George Champion Modern Shop features 20th century American, Italian, and Scandinavian furniture and objects.
The Hidden Acorn

21. Take advantage of seasonal outdoor restaurants. West Shore Seafood in Bantam has mouthwatering seafood and a garden area or seasonal tent. If you like a drive-up experience, Gooseboro Drive-In in Bantam serves up traditional food like hotdogs and hamburgers. Popey’s in Morris is a local favorite with picnic tables and glider swings. Head to New Milford for Clamp’s–a traditional hamburger stand with a casual atmosphere. Newly opened, Pasture in Morris is Litchfield County’s first food park combining a BBQ + Taco truck with a wickedly creative ice cream business and wood fired mobile bar. 

22. The Institute for American Indians in Washington offers many educational programs to engage learners of all ages and create a deeper understanding of Native American history.

23. Immerse yourself in creative collaborations and conversations at Spring Hill Arts Gathering multi-day event, June 22-25. There will be many different public programs that connect artists with nature

24. Spend the day at a beautiful vineyard. Litchfield County has numerous vineyards to enjoy. Bring a picnic blanket and some chairs and relax while sipping on wine and watching the sunset. Check their websites for special live entertainment events. Here are just a few: Walker Road Vineyards in Woodbury; Sunset Meadow Vineyards in Goshen; Hopkins Vineyard in New Preston; and Hawk Ridge Winery in Watertown.

Hopkins Vineyard

25. Let’s go antiquing! You are bound to find something you love at one of these popular places:

26. If you love beautiful landscapes, be sure to visit the Hollister House Garden in Washington. The gardens, open to the public, complement the 18th century house, barns, and outbuildings.

27. Starting June 21st, kids can explore their creativity at the Kids Lego Club offered every Friday afternoon from 1:30-2:30 pm at the Oliver Wolcott Library!

28. Find that perfect piece you’ve been searching for at a local Flea Market. Be sure to check each website for updated information. Elephant’s Trunk in New Milford; Woodbury Flea Market; and Bethlehem Indoor Flea Market.

29. Gardening enthusiasts, stop by White Flower Farm in Morris. Not only do they have a variety of plants but they have beautiful display gardens to inspire you.

30. Pick your own berries and fruits at March Farm in Bethlehem and grab a fresh baked pie at their farm store & bakery.

March Farm

31. Kayak and paddleboard in Bantam Lake, the largest natural lake in Connecticut covering 947 acres. There are two launches, Beverly’s Marina at the corner of Rt. 209 and Palmer Road in Morris, or White Memorial Family Campground Launch.

32. Visit Kent Falls Brewery, part of Camps Road Farm—a 50 acre diversified farm in Kent. The most recent addition to their operation is their tasting room. Visitors can learn about the process in detail while sipping on some great beer. Children will love visiting with their pigs and chickens.

33. Spend a day at Lime Rock Park in Lakeville. Sign up for a driving program or check out their special events such as their Historical Festival 41 held over Labor Day weekend.

34. Cool off after a hot summer day at Farmington River Tubing and enjoy a 2.5 mile ride down the wild and scenic Farmington River.

35. Community Table located in New Preston is recognized for its acclaimed food and cocktails, is a great place to meet with friends, celebrate, or dine solo this summer. Don’t miss Burger Night on Monday nights!

36. What’s better than warm summer nights accompanied by live music? March Farms Friends Friday will be nights you don’t want to miss out on.

37. Stop by a local farmers market. We have many in our county!

38. Picnic at Topsmead State Forest in Litchfield. Topsmead offers 510 acres of forests and meadows. There is plenty of space for social distancing, walking, picnicking, and bird watching at this beautiful former estate of Edith Morton Chase.


39. Spend a day in the town of Litchfield shopping and make sure to stop in at R. Derwin Litchfield, known for their fine clothing for men and women;  J. McLaughlin for seasonal clothing with a casual, classic style; Oliphant for beautiful summer clothes, furniture, and house decor; Milton Market for beautiful home goods, art, and fresh flowers; Ideal Jewelers and Lawrence Jeffrey Estate Jewelers for jewelry. Afterwards, refresh with a fine meal from the renowned West Street Grill, @ the Corner, The Village Restaurant, or DiFranco’s Restaurant.

40. Calling all Gilmore Girls fans, join a stitch circle or book a private lesson at Stars Hollow Yarns in Washington, a yarn shop inspired by the community in the fictional town of Stars Hollow.

41. Check out the hamlet in Warren. Go shopping at WKND in Warren, filled with upscale men’s and women’s clothing, children’s clothing, and gifts for home. There is something for everyone. Afterwards, enjoy a bit of lunch outside at Warren General Store.

42. The land behind the Tapping Reeve Law School is the perfect place for relaxing and learning. It features a children’s garden, education pavilion, small orchard, and more. The meadow is open from dawn to dusk.

43. Taco Heaven at El Camion in Woodbury! Voted best in CT by numerous publications and one of the best places to get tacos in the county—their tacos are made with locally grown produce and fresh ingredients for healthy and original Mexican food.

44. What better way to relax than by cozying up with a good book from a locally owned bookstore? Spend time browsing in Hickory Stick Bookshop in Washington Depot or House of Books in Kent.

45. Go fly fishing on the Housatonic. This river is known to be the perfect spot for brown trout and rainbow trout fishing. Call Housatonic River Outfitters for tours and equipment.

46. Visit a covered bridge. We have beautiful historical covered bridges in Litchfield County, and both offer great hiking trails nearby. Please note that it is unsafe to go into the water at any of these areas due to strong currents.

47. Check out Mine Hill Distillery in Roxbury and enjoy a craft cocktail while learning about the history of the Roxbury Station property during the Industrial Revolution.

48. Take a day to stop by the amazing art galleries we have in our area. KMR Arts, The Hen’s Nest, Eckert Fine Art, Judy Black Memorial Park, and Washington Art Association in Washington Depot; Jennifer Terzian Art in Litchfield; James Barron Art, Carol Corey Art GalleryCraven Contemporary, Kenise Barnes Fine Art, and Morrison Gallery in Kent.

Kenise Barnes Fine Art (Photo Credit: Jonathan Beckerman Photography)

49. Looking for that perfect piece of jewelry for yourself or someone else? Check out Hays Worthington in Washington, Ideal Jewelers and Lawrence Jeffrey Estate Jewelers in Litchfield, Robertson Jewelers in New Milford, and Onyx II Jewelers in Watertown. While some have estate jewels, each is sure to have something you’ll love, or will custom make a special piece.

50. Lastly, a summer in Litchfield County isn’t complete without ice cream from Arethusa in Bantam, Peaches ‘N Cream in Litchfield, Popey’s in Morris, The Roxbury Market, and Marty’s Cafe in Washington Depot. Kimberly Farm, in New Milford, has a newly opened ice cream stand serving their own ice cream!

51. Stop by the Torrington Watermelon Festival & Flea Market on August 3rd for a fun day of great food, refreshing drinks, lively music, and more! Make sure to watch Resty Nombrado carve the most amazing creations out of fresh watermelons!

52. Hiking, camping and fishing at Black Rock State Park in Watertown, Hiking, fishing and the Lookout Tower at Mount Tom State Park in Litchfield,  and camping at Lake Waramaug State Park in New Preston.

53. Take a stroll through the Action Wildlife Foundation in Goshen and observe wildlife from six of the seven continents.

54. Evergreen Berry Farm in Watertown—pick your own black raspberries, blackberries and blueberries. Try berry juice pops and iced teas created from berries, herbs, and flowers grown on the farm.

55. Visit Beckley Furnace in Canaan; historical, educational, and beautiful place for all age groups. Learn about the furnace, picnic with the family, and surrounding areas offer wonderful photo opts.

56. Take a journey through the Naugatuck River Valley with the Railroad Museum of New England in Thomaston. Different train experiences are offered throughout the seasons.

57. American Mural Project in Winsted (Winchester) is a tribute to American workers and sheds light on what aspects have defined the country over the last century. It now serves as a way to educate and inspire people of all ages the many ways they can add to American culture.

American Mural Project

58. Norbrook Farm Brewery in Colebrook is fun for the whole family, with their 450 acres of land they offer hiking trails, mountain bike trails, and so many more activities. Try out their farmhouse style beer, lagers and ales.

59. Golf season is back! Take a swing at a few golf courses in Litchfield County. Fairview Farm Golf Course in Harwinton, Crestbrook Park Golf Course in Watertown, Stonybrook Golf in Litchfield.

60. Take a family trip to Highwire Deer and Animal Farm in Woodbury, where you can feed, visit, and touch some exotic and non-exotic animals.

61. Visit local parks in the area such as Field 1- Veterans Memorial Park in Watertown. It is part of the Where Angels Play Foundation and the playground was built in honor of Dawn Lafferty Hochsprung, Sandy Hook Elementary School’s Principal.

62. Take a 3 hour long hot air balloon ride with Aer Blarney Balloons in Bethlehem!

Aer Blarney Balloons

63. Looking to enjoy some time away from the city? Take a trip to Southwind Farms in Watertown, the 27 acre Alpaca farm with 50+ alpacas.

64. Calling all social media stars! Saville Dam in Barkhamsted offers picture-perfect spots!

65. Attend the annual Podunk Bluegrass Music Festival in Goshen  from August 8-11! Listen to outstanding bluegrass acts, participate in family fun activities like tie dying and scavenger hunts, shop their craft and merchandise area, and eat some delicious food from a variety of options!

66. Support volunteer firefighters and EMS members at the Bridgewater Country Fair in Bridgewater from August 16-18. Stop by the many food tents serving tacos, ice cream, and slow cooked chicken and start the weekend with the Annual Bridgewater Fair Parade!

67. Take a trip to Guy Wolff Pottery in Bantam for some wonderfully unique pots made by local artisan Guy Wolff, who focuses on the architectural integrity of the pot and knowledge of the materials being used.

68. Try out a new hobby that is fun for all ages! Litchfield County offers many opportunities for horseback riding. Check out Lee’s Riding Stables in Litchfield, Fox Crossing Equestrian in Morris, and Daffodil Hill in Woodbury.

69. Take a break from everyday life and take a walk into nature. Explore the 106 acres of Boyd Woods Sanctuary in Litchfield. The Sanctuary is home to a diverse habitat. Enjoy the hiking trails and take in the wildlife.

70. Grab some food and beverages and make your way over to Litchfield County Axe House in Thomaston for a fun night with friends or families. Uniquely, Litchfield County Axe House also has a mobile axe-throwing trailer for rent.

71. Visit Thorncrest Farms and Milk House Chocolates in Goshen, to buy homemade chocolate and visit the cows who make it possible!

72. Feeling creative? Head on over to Glazey Dayz in Watertown and paint your own pottery or glass. Perfect for birthday parties, a trip with friends, or even family gatherings.

73. Spend a few nights or longer camping at Gentile’s Campground in Plymouth. The campground offers hot showers, propane gas, flush toilets, a basketball court, and many more activities.

74. Head on over to Infinity Music Hall and Bistro in Norfolk for some live music and stand up comedy shows.

75. Get your fitness on this summer with Blue Boy Boxing Club in Thomaston. They offer self defense classes for kids and adults. They also specialize in Parkinson’s boxing fitness!

76. Looking to connect with local wildlife? Take a self-guided walk or book a tour of the Ripley Waterfowl Conservancy in Litchfield. Boasting more than 60 species of waterfowl, the conservancy welcomes visitors to admire their beauty!

Ripley Waterfowl Conservancy

77. Sit back, relax, and enjoy the show at Bantam Cinema & Arts Center, a non-for-profit in a historical building offering a diverse program of film, theater, music, and visual arts. After, head right next door to Wood’s Pit BBQ & Mexican Cafe to enjoy one of their many delicious meal options!

78. Grab a delicious meal from the food trucks at the Pasture in Morris! Newly opened, this location is Litchfield County’s first food park run by South Farms!

79. Shoot for the stars at the J. McCarthy Observatory in New Milford! Visit them for their monthly “Star Parties” and other events, or book a private visit!

80. Take a walk through history in one (or all!) of Litchfield County’s house museums! Here are a few: Glebe House Museum & Garden and Leroy Anderson House in Woodbury; Bellamy-Ferriday House and Garden in Bethlehem; and Hotchkiss-Flyer House Museum in Torrington!

81. Join the Arts Alliance of Woodbury for their 4th annual Arts Walk on July 20th and August 17th from 1-5 pm! Stroll along Woodbury’s picturesque Main Street and admire the artwork of many local artists.

82. Looking for some R&R? Head to The Spa at Litchfield Hills in Litchfield, Winvian Farm Spa in Morris, or Mayflower Inn & Spa in Washington for some world-class pampering. 

83. Prepared to be wowed by the live productions put on by the theaters in Litchfield County, offering performances from The School of Rock at The Warner Theater in Torrington to The Prom! At Sharon Playhouse in Sharon! Among many others, also offering fantastic fine arts performances are FineLine Theatre Arts in New Milford and Thomaston Opera House in Thomaston

84. Jam out to some tunes at the Jazz at Music Mountain Opening Concert in Falls Village! Purchase tickets to see the Bobby Sanabria Quartet for Afro Cuban Jazz Night!

85. Gather some friends to sip some delicious wines at Spring Hill Vineyards in New Preston during their wine tastings!

Spring Hill Vineyards

86. Stop by The Smithy Cafe in New Preston for the Music on Main Concert Series. Live music by local musicians every Thursday in July and August! Free entry and BYOB!

87. Calling all history buffs and those interested in local history! Founded in 1751, Litchfield county abounds with fascinating history. Here are some of the towns with historical societies that invite you to visit them for their historical buildings, artifacts, events, or information: Barkhamsted, Bethlehem, Bridgewater, Colebrook, Cornwall, Falls Village, Goshen, Harwinton, Kent, Litchfield, New Milford, Norfolk, Plymouth, Salisbury, Sharon, Thomaston, Torrington, Warren, Watertown, and Woodbury.

88. Take a bite (but probably more) of fresh bread from Bantam Bread Company in Bantam! Pick from a variety of loaves and grab something delicious from their sweets and desserts! Dog lovers can also purchase treats for their good boy or girl!

89. Start your morning right at Jackie’s Restaurant in Bantam – whether in the mood for a stack of fluffy pancakes or a stacked breakfast sandwich, you’re sure to leave with a belly full of delicious food.

90. Attend a “Weed and Wine Wednesday” at Judea Garden in New Preston. Clear your Wednesday night to weed the vegetable beds at Judea Garden alongside fellow gardeners! You’re sure to be thirsty after that…well it’s a good thing you get to enjoy a free glass of wine next!

91. Sip on some delicious wine and enjoy live music on Saturdays and Sundays at Hopkins Vineyard in Warren! Tickets are free, snacks are available, and music is plentiful…what could be better than that!

92. Get some hands-on experience with one of Litchfield County’s many pick-your-own farms! Here are some to look out for: Angevine Farm in Warren, Averill Farm in Washington, Bunnell Farm in Litchfield, Ellsworth Hill Orchard and Berry Farm in Sharon, Evergreen Berry Farm in Watertown, Harris Hill Farm in New Milford, Litchfield Hills Blueberry Farm in Plymouth, Maple Bank Farm in Roxbury, March Farm in Bethlehem, Starberry Farm in Washington Depot, and Tonn’s Orchard in Terryville.


Fort Hill Farm (Photography credit: Ethan Ash)

93. Need a mid-day sugar boost? Grab some candy at Litchfield Candy Company in Litchfield or Sweeets in New Preston!

94. Want to spend a day like Rory and Lorelei from Gilmore Girls? Hang out in Washington, CT to visit the town that inspired the show writer to create Stars Hollow. Here are some places around town that are reminiscent of the show’s setting:

95. Attend the Bethlehem Fair in Bethlehem! You can look forward to a great variety of exhibits, music, rides and food, from roast beef to fried desserts!

96. Cool down with Connecticut Watersports on Bantam Lake! Offering waterskiing, wakeboarding, tubing, kayaking, and more, there is no shortage of fun summer activities to look forward to!

Connecticut Watersports

97. Decorate your home with some of the beautiful flowers and plants grown by farms in the area: Falls Village Flower Farm in Falls Village; Northern Farm and Flowers in Goshen; Anderson Acres Farm in Kent; and Lindell Flower Farm in New Hartford.

98. Pick up some fresh fruits, vegetables, milk, cheese, jams and more from the farm markets and stands in the area. Here are just a few of the many: The Local in Cornwall; The Smithy in New Preston; Freund’s Farm Market in East Canaan; Rustling Wind Creamery in Falls Village; Barden Farm Market in New Hartford; The Village Farm in Gaylordsville; and Maple Bank Farm in Roxbury.

99. Spend a day exploring Kent Barns in Kent; enjoy the shops, galleries, restaurants, and other businesses occupying more than a dozen buildings, including six restored or rebuilt historic barns!

100. Take a break from your everyday and stay at Twilight Dreams Farm in Roxbury. Not only is this farm an AirBnB superhost with 5.0 stars, but it offers the unique opportunity to stay on a working farm with a farm stand on site. Twilight Dreams Farm is also close to popular hiking trails, family day trips, restaurants, and other outdoor activities!

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