Chester Inn


25 Years of Gratitude

As we prepare to turn our seasonal pumpkins into pie for Thanksgiving dinner for the 25th time, it is a reminder to us to be truly grateful….

For our guests who come to Chester to be still and enjoy nature.

For our guests who need a break from hectic lives.

For our guests who enjoy sharing their lives with us.

For our adventuring guests who climb up and down Crabtree Falls.

Yes, and for our guests who need a little extra TLC.

In short, it is a joy to celebrate 25 years of innkeeping and to look forward to our next guests.

Happy Thanksgiving!

Harvest time is coming!

It’s hard to believe that fall will be here shortly, but it is definitely on the way. Join us the weekend of September 20th as we enjoy all of the exciting offerings that Monticello hosts at their annual Heritage Harvest Festival. In addition to all of the wonderful sessions about winter gardening and saving seeds, as well as some early holiday shopping, you’ll find this year has some new flavors as well. From dialogues about how food justice shows up in our neighborhoods to a live taping of Sporkful, the #1 food podcast in America, there’s something for everyone here. Jonathan Till, the executive chef of the wildly popular Evening Star restaurant in Alexandria will even be giving a talk! Rooms are available, and Monticello is a quick drive down beautiful Route 20! For more information, visit .

Tastings and talks at Monticello’s Heritage Harvest Festival

Chester…where the wildlife comes to you!

We are so privileged to share our seven acres of aboretum grounds with all variety of flora and fauna. Often, we have to look to find that rare migrating bird, a family of bunnies crossing the yard, or a glimpse of a deer right at the edge of the woods, coming out for an early evening treat. But last night, we were treated to our very own display of beautiful deer who were none too shy. After a hot day, they had clearly come out for a walk with their fawns! We were sitting on the North Porch, overlooking the pond, and lo and behold, they appeared. We are so close to Charlottesville and all it has to offer, and yet in the middle of the country where wonderful things like this happen. Come and visit us; maybe you’ll get a visit too!

The fawns
Mama standing watch
No shyness here!

Car Show for a Cause!

Do you have a car you’ve been waiting to show off? Or perhaps a bit of car envy? Join us for the 2019 Festival of the Wheel on September 1st from 10-3, held at the Boar’s Head, just a 20 minute drive from Chester. All proceeds benefit the UVA Cancer Center, so it’s for a great cause too. Book your Labor Day weekend reservations with us and visit for more information about the show!

It’s almost time for UVA Football (and we’ve got a deal for you)!

Here’s a special deal for you on tickets! Book your reservations here now and get $15 tickets to the game on Friday, September 6th!

Virginia Football opens the 2019 season on the road on Saturday, Aug. 31 against ACC rival Pitt. The Hoos return to action for the 2019 home opener at Scott Stadium on Friday, Sept. 6 against William & Mary. Kickoff is set for 8 p.m. under the lights!Click here and use promo code PAINTTHETOWNORANGE to get $15 lower level tickets for this game – a savings of over 50%!

We’re all about singing at Chester, and even more so about unity in our community! Join the Martin Luther King Jr. Community Choir for the “C’ville Sing Out” on Saturday, August 8th. Your $5 ticket gives you access to a rehearsal at 10 a. at the Charlottesville High School, and the main event at the Pavilion on the Downtown Mall where you can perform with the choir! Visit for complete details.

After the Storm…

The thunder and lightning have abated…all is calm again. Through the ancient trees at Chester B & B there steals an almost surreal light.

I think Claude Monet would have delighted in the shadows and subtle shadings all too rarely observed by most of us.

Summer Soltice Lilies at Chester B & B

Years ago when we came to Chester in Scottsville, we decided to use the lily for our logo. Over the years we have planted many varietals on the grounds – yellows, deep reds and oranges. They all have a special quality about them as they reappear in the gardens year after year. The wild orange lilies that grace the Virginia roadsides have a considerable stake on the Chester grounds. A dear friend and forever Virginian calls them “johnny house lilies.”

Our favorite has become the Lady Rebecca Staunton lily – yes, it was developed in honor of the city of Staunton, Virginia. She is always at her best for the Summer Solstice – perhaps she enjoys that very long day to display her intense blossoms.

The only downside to loving lilies is that our small group of resident deer also enjoy them. The buds seem to be a favorite “midnight snack.” We just hope their snack is as much a treat for them as the blossoms are for us.

At last…

The gardens are looking great, the lawn is mowed. Finally, there is a bit of time to relax and take stock of life here at Chester. Living near or visiting Scottsville is truly a sensory delight.

Views of the majestic Horseshoe Bend on the James River, blooming gardens, an eagle soaring overhead, and stars in the nighttime sky are only a few of the visual opportunities.

The scents of magnolias and honeysuckle, a hint of smoky bar-b-que in the air, perhaps coffee brewing somewhere nearby in the early morning, or event the smell of a gentle rain shower sprinkling the herb garden are welcome.

What a treat to waken to the song of a lark, to listen to tree frogs peeping, bull frogs croaking and a cacophony of bird calls. Yes, and there is also the delighted barking of a dog out for a ride in a pick-up truck.

This is life in Scottsville – no huge rush hour, only five minutes to get that extra bottle of milk, friendly restaurants nearby, a local brewery and coffee shop for break times, yoga classes, spa treatments and a gym are available locally. Walking trails abound , river activities are easily accessible. All come infused with a sense of history that reaches back to the beginnings of our nation.

Just a short drive from town are vineyards – too many to visit in even a week. There are so many opportunities to taste the wines of our area and enjoy a bit of cheese or some tapas surrounded by vast mountain views.

One could go on and on if time permitted…right now the animals need feeding, and the guests are approaching the door. It will be a joy to welcome them and share our special place for a time.

Independence Day Events

Whether you live in Charlottesville or will be visiting during Independence Day, Charlottesville offers many events to make your 4th of July unforgettable!

Highlands Independence Day Concert and Celebration

Charlottesville 4th of July events

James Monroe’s Highlands will feature an Independence Day Celebration and Concert, with free access to the historic grounds all day, family games and activities, and a free concert by the Heifetz International Music Institute! The concert will feature a classically-inspired ensemble that will appeal to all ages. Bring a picnic or grab lunch from the Museum Shop, and relax on the lawn with this Independence Day Concert! – Learn More

Monticello Naturalization Ceremony
4th of July Events in Charlottesville

Monticello will host their Annual Naturalization Ceremony and Independence Day Celebration, the morning of the 4th. The Naturalization Ceremony attracts visitors from around the country and welcomes new citizens to our great nation! Monticello will also offer free tours of the historic home after the event. – Learn More

Patriotism in the Park
Charlottesville 4th of July events
Charlottesville’s CBS19 News will host the “Patriotism in the Park” at McIntire Park. The event will feature family-friendly fun music and entertainment, activities for kids of all ages, and local food vendors! A spectacular fireworks show begins just after dark!
– Learn More


Scottsville 4th of July Events
Charlottesville 4th of July events
Our local Scottsville also offers 4th of July festivities! The events start in the morning with the Main Street Parade and continue to the afternoon with the 4th of July fair at Dorrier Park, with live music, bounce houses and food vendors, and of course, Fireworks over the James River finish off the night!


If you are visiting Charlottesville any time during the summer, Chester Inn Bed and Breakfast is the perfect home base for all your activities! Or if you live in Charlottesville, take a wonderful break from the ordinary. With a quaint downtown and the beautiful James River, Scottsville and Chester Inn are an ideal getaway for your summer break!