Homestead Inn

5 Elm Street, New Milford, Connecticut 06776
Innkeeper(s): Francesca Morrissey
  • Introduction

    The Homestead Inn at New Millford Connecticut

    This lovely corner of the Litchfield Hills offers something for everyone: fine dining; great antiquing; a wealth of trails for hiking, running, and cycling; lakes and rivers for boating, beaching, rowing and fishing; slopes for skiing and snowboarding; parks and playgrounds; local farms with seasonal fruits for the picking; year round festivals that showcase art, dance, and music; and so much more! And for those who don’t want to stray too far from the Inn, downtown New Milford is just a short walk away. Main Street, Bank Street and Railroad Street are lined with shops and offer a wealth of restaurants – Italian, German, Mexican, Cuban, Chinese, and Irish, just to name a few. Enjoy a self-guided tour of the town’s antique homes, buildings, and churches; take in a movie at the Bank St. Theater; delight in the many summer concerts on the Green or simply take a stroll around the Canterbury School campus where both President John F. Kennedy and Paris Hilton were once students.

    The Homestead Inn common roomThe Homestead Inn dining

    Your visit with us includes our hearty continental breakfast served every glorious morning in our Victorian dining room. Enjoy a variety of yogurts, cereals, oatmeals, jams, cheeses, fruits, breads, muffins, juices, teas and coffee. And don’t pass up the opportunity to try our signature dishes: fluffy egg bakes, bread puddings, French toast bakes, homemade breads and of course, Bill’s (Not So) Secret Waffles which are talked about around the globe.

    The Homestead Inn living roomOutdoor attractions in our area include Candlewood Lake, Lake Waramaug, the Housatonic River, the Shepaug River, Lake Lillinonah, White-Memorial Coservation Center & Museum, Mt. Tom State Park, the Appalachian Trail, the Western New England Greenway (cycling), Mohawk Mountain Ski Area, Butternut Ski Lodge, the Elephant's Trunk (largest outdoor flea market in CT), Candlewood Valley Country Club (golfing) and Lime Rock Race Track.

    Come stay with us to be in the center of it all!

  • Insider's Info

    Travelers are always looking for memorable and relaxing experiences. Let’s discover more through the words of our innkeepers. Many thanks to Francesca Morrissey for sharing her own secrets with!
    Why do most travelers stay at your inn?

    Most of our guests are "repeaters," many of them I would even consider "regulars" and really are more like family. We love seeing parents dropping off at,  visiting or picking up from one of the many area private boarding schools and in the warmer months, from summer camps like Bucks Rock. We have quite a few guests who frequent us when in the area for business or when visiting local residents.

    Name 3 characteristics that set you apart.

    The waffles, the location and the hospitality of our staff, particularly of Owner Sherry Greenman and Innkeeper Francesca Morrissey.

    If someone has never been to your town, what is the #1 reason to come visit?

    Are you kidding?! It's impossible to name just 1!

    What’s the best compliment you have ever received about the inn?

    "What a great little Inn! Best waffles ever! Private bathroom. Francesca is hip & amazing! Good movies. So comfy & quiet. 5 out of 5 stars. Thank you!!!"

    What’s the best kept secret about the area?

    Sega Meadows Park, located at 120 River Road. This compact, riverside nature preserve includes ancient forest, a meadow, a fishing pond, and a spectacular view of the Housatonic River.

    If a traveler is staying at your inn for 4 nights, what should he/she do in the area?

    Shop, hike, bike, run, swim, go boating, hang at the beach, row, fish, ski, snowboard, go apple or berry picking, enjoy a free concert on the Green, attend an area summer fair or a fall harvest festival, find and cut down a family Christmas tree, visit a museum, do some antiquing, ride the train to NYC and spend a day in the big city, take a scenic drive, go for a walk, read, relax, sleep, eat, drink, be happy ... repeat!

    Is there anything within walking distance of your inn?

    We are right downtown. There are shops and boutiques, a four screen movie theater, a book store, a coffee house, several sweet shops and too many restaurants to count.

    What is your favorite restaurant/food in the area?

    Sherry and I both have a hankering for Italian, but we differ on which of the 3 within walking distance are the best.  Sherry's vote goes to La Piccolina while mine goes to Lucia's. Then again, if I'm in need of a margarita, I'm hittin' Salsa. And if I want some entertainment with my food and drink, then I'm hanging at O'Connors Public House on a Monday so I can drink some awesome beers, eat beer battered pickles (they're so much better than they sound!) and play DJ Trivia.

    Any good area guides/websites that travelers could reference?

    How many rooms does your inn have?


    Do you accept pets?

    We accept pets in six rooms.


  • Famous Guests

    The Homestead Inn has a long and successful history of providing lodging to the rich and the famous. And, unlike other local lodging establishments, all of the following guests not only spent the day at the Homestead Inn, they slept here too! The following is a list of some of those that have stayed at the Homestead Inn.

    1928 - 2003

    BBO The Homestead Inn porch

    • Joe and Rose Kennedy, as well and most likely the children, especially JFK
    • Marilyn Monroe, when engaged/married to Arthur Miller
    • Vladimir Horowitz, Pianist
    • Leopold Stowkowski, Composer
    • Frederick March, Actor (Inherent the Wind with Spencer Tracy) 2 Oscars for Best Actor
    • Philip Kappel, Artist
    • Dr. Warren Weaver, Scientist, Pioneer in Machine Translation, died in New Milford in 1978
    • Edith Newton, Local Artist

    2003 - Present

    • Charles E. Schumer, United States Senator, NY
    • Mike Rowe, Media Personality, "Dirty Jobs"
    • Butch Patrick, Child Actor (Eddy Munster)
    • The Batmobile, One of the 6 Original Batmobiles
    • Pepe Romero, Classical Guitarist
    • John Tesh, Televison Presenter and Radio Host
    • Beverley Owen, Original Marilyn on the Munsters
    • Bob Margolin, Blues Guitar Player and Singer
    • Pat Martino, Jazz Guitarist
    • Joseph Greico, Artist
    • Manuel Barrueco, Classical Guitarist
    • Kenneth Merten, Ambassador to Croatia
    • Redondo Blackman, NBA All-Star
    • M. A. Batio, Rock Guitarist
    • Lloyd Garrison, Artist
    • Hubert Sumlin, Blues Guitarist
    • Steven Banks, Writer, actor (Spongebob SquarePants)
    • Teller, Performance Artist (Penn & Teller)
    • Reuben Wilson, Boxer, Actor & Jazz Musician
    • Pilobolus, many talented dancers & technicians
  • Things To Do


    Golf Courses

    Candlewood Valley Country Club:

    401 Danbury Rd, New Milford, CT, 860-354-9359 Golf at Candlewood Valley Country Club is being met by our professional starters who effortlessly get you situated for your round, before you check in at our Golf Shop. It is our PGA Golf Professionals who will take the time to make sure you are on your “A” game. It is our Superintendent and his dedicated team making sure the tees, fairways, greens, and grounds are in superior condition.

    Lakes & Hiking

    Candlewood Lake:

    Candlewood Lake has been the lakeside recreation hub in Connecticut since the 1920s. It is the largest lake in the state and one of the biggest man-made lakes in the country. Candlewood Lake offers nearly 90 miles of shoreline that run through five quaint towns, including New Milford. Candlewood Lake is a favorite destination for waterskiing, wakeboarding, boating, and year-round fishing. Scuba divers will find an exceptional experience at Candlewood Lake. Remains of historic towns that dotted the area prior to the lake's construction can be explored, including old roads and covered bridges. Echo Bay Marina, Gerard's Waters Edge Marina and Candlewood East Marina are full-service facilities located at various points around Candlewood Lake.

    Mt. Tom:

    3 miles west of Bantam off Rte. 202. The stone tower at summit of Mt. Tom 1,325 ft. is a favored destination among hikers. The tower trail is about 1 mile long. Picnicking, swimming, hiking, stocked fishing, boating/non-motor, scuba diving, and ice-skating. Charge: daily. Park Office: (860) 868-2592.

    Lake Waramaug:

    Off Rte. 45, New Preston. Scenically, few bodies of water in CT. can rival the unspoiled beauty of Lake Waramaug. 77 campsites, bathrooms, showers, concession, swimming, scuba diving, picnicking, fishing, field sports, hiking, ice skating, camper nature program, mountain biking, home to an annual triathalon and ultra marathon. Charge: camping, weekends and holidays. Campground Office: (860) 868-0220 (May 15-Sept. 30). Park Office: (860) 868-2592.

    White Memorial Conservation Center

    More than 35 miles of trails, through varied terrains, are open year-round for hiking, biking, cross-country skiing and horseback riding. There are also interpretive nature trails and a boardwalk trail for observing the extensive bird life found in a wetland environment.
    80 Whitehall Road, Litchfield, CT 06759. Phone- 860-567-0857.


    The Elephant's Trunk

    The Elephant's Trunk, CT's largest outdoor flea market, is located on Route 7 in New Milford, Connecticut, just over the Brookfield line. The 55-acre parcel sits vacant most of the week, coming alive each week on Flea Market days! The field is boarded by a large looming hill at the back and a long row of trees to the south. The front of the property borders Route 7, with the east bordering Candlewood Lake Road South. The spring, summer, and autumn seasons often find deer grazing in the back field, geese flying overhead, and birds singing in the woods. The grassy field is marked with lime dots, designating the borders of the vendor spaces. It was Robert Frost who said, "good fences make good neighbors", so we mark our spots to encourage good neighbors. Autumn is a special time, painting a wonderful splash of color on the hillside-- a tribute to living in New England. Aside from nature's gifts, our ambiance is enhanced by the friendly, loyal dealers who come weekly, selling a variety of wares. Equally as important are our loyal and friendly buyers, many who have been buying here for years. It is this chemistry which makes The Elephant's Trunk New England's most exciting market.

    Bob Kretchko Antiques

    Located just off the Historic Village Green (and one block from the Homestead). We pride ourselves on providing customers with quality antiques and personal service. We deal in fine quality antiques Victorian all the way through to mid century. We buy and sell antique and vintage collectibles such as Advertising signs, 19th Century Photography including cameras and viewers, Sterling Silver, Clocks, Bronzes, Paintings, Fine Glass and Porcelain, and Antique Coin Operated Machines. We are available for both buying and selling by appointment.  Contact Bob Kretchko at 860-354-4759.

    Apple & Pumpkin Picking, Corn Mazes & Hay Rides

    Paproski’s Castle Hill Farm

    Located in Newtown, Connecticut, it has been owned and operated by the Paproski family for four generations. Currently a retired dairy farm, Castle Hill Farm was once the second largest supplier of dairy products in Fairfield County! 

    The farm is approximately one hundred acres in size and is known to be a fun and educational attraction to many in the fall season. Castle Hill Farm is the proud owner of Paproski's 4 acre Pumpkin Patch and 7 acre Corn Maze. Visit us in the fall for Hay Rides, Pick-your-own Pumpkins, Our Petting Zoo, Corn Maze, Pony Rides, and much more!

    Averill Farm

    A family farm, which has been operated continuously by the Averills since it was purchased in 1746 from the holdings of Chief Waramaug.  For many years it was a dairy farm.  Today, the 260-acre property is primarily a fruit orchard, but also produces hay and Christmas trees.  Sam Averill, of the ninth generation, runs the farm with his wife Susan, son Tyson (10th generation!), and several  full and part-time employees.

    The apples and pears are grown in the 30 acre orchard and are sold both as picked fruit and pick-your-own (PYO).  Some 100 varieties are grown, about 20 of which are available for customers to pick.  Early apples come at the end of July or beginning of August and are sold either at farmers markets or self-service in front of the "Homestead". The PYO season begins mid August, when the orchard stand opens, and stays open seven days a week, 9:30am to 5:30pm, or dusk (after the time change), until Thanksgiving.

    We sell our own cider, apple cider donuts, cut flowers, and homemade the old-fashioned way, jams and jellies. We also sell locally-sourced pies, pumpkins, gourds, Indian corn, mums, maple syrup, honey, cheddar cheese, garlic, potatoes, some tomatoes, and gifts.

    After Thanksgiving, we sell fruit, cider, and Christmas trees from our homestead until the Christmas Tree season ends on December 24.  After that, any remaining apples are sold from cold storage.

    Wineries & Vineyards

    Haight-Brown Vineyard takes great pride in being part of a wine industry in Connecticut that is steadily building a reputation in the eyes of those who enjoy the world’s fine wines.

    Haight Vineyards is Connecticut's oldest winery, opening its doors in 1975. In 2007, the winery was purchased by Amy Senew and renamed Haight-Brown Vineyard. The winery is located in Litchfield, CT in the northwest part of the state.

    Haight-Brown Vineyard owns and leases over twenty acres for its winery and vineyards. The vineyard grows vinifera and hybrids including Chardonnay, Chardonelle, Marechal Foch, Dechaunoc, Marquette, and Seyval Blanc. Its current growing capacity has the ability to produce yields upwards of thirty-five tons annually.

    Haight-Brown Vineyard, 29 Chestnut Hill Road Litchfield, CT Phone: 860-307-5426

    Miranda Vineyard

    The Mirandas’ handcrafted vintages are produced using traditional European methods passed down through the generations, combined with modern scientific advances. Come visit the picturesque vineyard located in the rolling Litchfield hills. Bring a picnic and friends! Take in the scenery and enjoy a glass of their unique award-winning wines. There is always something happening at Miranda Vineyard, whether it is live music on the weekends, showings by local artists or special events like wine & chocolate pairings, educational classes or a semi-annual Luscious Ladies Night. There is a wine and something special for everyone’s tastes. Miranda Vineyard, 42 Ives Rd., Goshen, CT

    White Silo Farm & Winery

    White Silo Farm is a small specialty winery. Our wine is produced and bottled on premises from farm grown fruit. Experience the charm of an earlier era by touring the old barn where the winery is located. Visit the fermentation, bottling, and corking rooms where the classical art of wine making has been preserved. Walk the fields or relax in one of our outdoor gardens. Guests are welcome to bring lunches. If you prefer, we also make gourmet box lunches and cheese plates. Advance notice is required for box lunches. Many of the winery’s visitors describe our farm and winery as a magical place. We think it is too!  White Silo Farm & Winery, 32 Connecticut 37, Sherman, CT 06784


  • We are AAA and Mobil Approved

    BBO The Homestead Inn roomYankee Magazine Travel Catalogue Bed and Breakfast Listing

    Fodor's Guide To New England

    Bed and Breakfast in New England

    America's Wonderful Little Hotels and Inns

    The Complete Guide to Bed and Breakfasts, Inns, & Guest Houses

    The Complete Guide to American Bed and Breakfasts

    Family Bed & Breakfast, and Country Inns of New England

    The Official Guide to American Historic Inns

    Frommers Bed and Breakfast -- New England

    The Best Places to Stay in New England

  • Testimonials

    BBO The Homestead Inn living room"This is like discovering GOLD!" - Joann L., New Jersey

    "Great place and great people. Francesca is the best! It's also nice to be the record holder for most waffles eaten. Thanks for everything!" - Sterling D., Minneapolis, MN

    "I will always remember your wonderful Inn and a lovely stay with my daughter. The Homestead is a real treasure! Francesca was a perfect hostess who made us feel so welcome, and it was wonderful having an opportunity to visit with other guests." - Maria B., Greensboro, NC

    "So lovely - every touch - cozy room, delicious breakfast & enjoyed relaxing on the porch - happy to find such a gem here in New Milford near my cousins. Looking forward to staying again!" - Tania S. & Luke J., Brooklyn, NY

    "We thoroughly enjoyed our stay here. We loved having the delicious breakfast every morning and the hospitality was off the charts!" - Leslie, Brett & Millie B., Denver, CO. "P.S. We'll be sure to tell our friends and family."

  • Directions

    From I-84 East - (NY, NJ, PA)

    1. In Danbury, take Exit 7 (Route 7 North) exit from left lane
    2. Proceed 13 miles North to New Milford (202 East joins 7 North after 4 miles)
    3. In New Milford, follow 202 East to the right and cross steel bridge (Bridge Street)
    4. Go to 3rd traffic light at Village Green
    5. Go left on far side of Village Green (Main Street)
    6. Go 3 blocks to top of green
    7. Turn right on Elm Street and Inn is on the left
    8. Made next left onto Treadwell and left into parking lot behind Inn

    From I-84 West - (Hartford)

    1. Take Exit 15 at Southbury
    2. Go right at bottom of ramp onto 6 and 67 North
    3. In 2 miles 67 North turns left. Follow 67 North approximately 18 miles to New Milford
    4. At Intersection with 202, turn right onto 202 East (Pass gas station on right)
    5. Proceed 3 blocks to light
    6. Make left on Elm Street, go one block
    7. Make a right on Treadwell and Inn is on the left
    8. Go left into parking lot behind Inn

    From 7 South - (Albany, VT, Western MA)

    1. At intersection with 202 in New Milford, go left on 202 East
    2. Go straight over bridge and up 3 lights to Village Green
    3. Proceed to top of green
    4. Turn right on Elm Street and Inn is on the left
    5. Made next left onto Treadwell and left into parking lot behind Inn

    From 202 West - (Litchfield)

    1. From light at intersection with 109 in New Milford (Valley Dodge on right) go 1 miles to next light
    2. Turn right onto Elm Street
    3. Go one block to Treadwell and make a right
    4. We are on the left, turn left into parking lot behind the inn