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Your Guide to Special Occasion and Holiday Wines

Wine is the perfect gift or accompaniment to any special occasion and is almost always welcome. The sheer variety of wines, though, also means it can be stressful to choose the “right” one for an unfamiliar scenario. Aside from bubbly at a New Year’s Eve party, some holiday wines aren’t so obvious. What’s the proper wine for Thanksgiving? For Easter?

Luckily, these aren’t life-or-death decisions. Plus, if you have a favorite wine, it’s absolutely okay to serve it whenever you like! Taking the extra step and pairing wines with events, parties, and times of year, though, is a wonderful way to expand your palate and feel connected to the season and those around you.

So, in the spirit of wine hobbyists everywhere, we’ve curated a list of events, occasions, and holidays alongside the wide array of Chiswell wines that complement them. If any of these ideas stand out to you, consider picking up bottles in advance before they’re gone. Better yet, join Crown Club to take advantage of monthly discounts and quarterly wine trios, ensuring you always have just the right bottle of Chiswell’s Virginia wine on hand!

Holiday Wines

A glass of Chiswell wine next to two baskets of Easter eggs.

Holidays are about togetherness and community, whether it’s a household, a family, or a whole party of folks sitting down together. The wine you serve helps set the tone for a gathering, so putting some thought into your choice of holiday wines is a fun way to make things a little more special for those you love the most.

Here are our ideas for some of the most popular holidays:

Thanksgiving

Everyone’s looking forward to pie! Have a dessert wine on hand, like our Sweet Albemarle Petit Manseng, to round out the meal.

Christmas

A savory winter roast deserves a hearty winter red. Consider a bottle of the 2021 Merlot.

Easter or Mother’s Day

Morning celebrations and brunches are excellent opportunities for mimosas. We recommend the Chiswell Sparkling Chardonnay.

Halloween

A dark, spooky, blood-red wine… preferably one that pairs well with chocolate, like the 2022 Chambourcin!

Valentine’s Day

The most romantic wine option will often simply be your partner’s favorite. For the adventurous, our 2021 Meritage is a nice complex wine to savor and discuss together.

Celebration Wines

Many celebrations in life warrant uncorking a bottle of wine. Birthdays, graduations, anniversaries, promotions, engagements…there are many predictable (and unpredictable) happy occasions that call for raising a glass. It’s nice to be prepared with the perfect accompaniment when the occasion arises. That way, when an announcement or accomplishment comes out of the blue, you’ll be ready to give it the proper toast.

A variety of wines in Chiswell glasses clinking “cheers!”

A bottle of sparkling wine is never out of place when congratulating or appreciating someone. Chiswell’s Sparkling Rosé is always in fashion, with a lively color and fruity nose that add personality and cheer to an event.

Alternatively, have a chilled, sippable white wine on hand, like a Chiswell Chardonnay. Light and easy to store, white wines are ideal for sharing at a smaller or more intimate catch-up about the good news. Seasoned chardonnay sippers may prefer the more rounded, early profile of our oaked 2020 Chardonnay, while casual wine enthusiasts might opt for our lighter 2021 varietal.

Outdoor and Daytime Gatherings

A family drinks wine and enjoys a charcuterie board outdoors, seated in Adirondak chairs.

Sharing a wine outside with friends can be a wonderful bonding treat, even at a barbeque or tailgate alongside burgers and chips!

Weather and setting can change a lot about what wines to enjoy. For grilling-focused events, a full-bodied red wine, such as Chiswell’s Cabernet Sauvignon, is a welcome companion to satisfying red meats. If you’re grilling on a particularly hot summer day, though, it might be more refreshing to make a cool, delicious sangria. Similarly, white wines are classics at garden parties and picnics, like Chiswell’s Sauvignon Blanc, as long as it’s warm and sunny.

Formal Occasions

Two Chiswell red wine glasses on a table with a bronze horse and a candlestick.

Sometimes, we need to impress people. Whether it’s a gift for a superior at work, something to bring to dinner with the in-laws, or a large event, it’s good to plan ahead. We want to get the “correct” wine to make a good impression, even if we don’t know someone’s personal tastes; one easy strategy to avoid decision paralysis is to look at a wine’s awards.

Many Chiswell wines are award-winning, including our multi-award-winning 2021 Meritage and 2021 Chardonnay, with silver medals in the 2024 Governor’s Cup and Monticello Cup. Quality is, of course, subjective, and even the most practiced sommeliers can disagree on matters of taste. Trusting an expert is still a good guide to a wine’s reputation and can take away some of the gamble in picking up unfamiliar wines.

Casual Get-Togethers

Three women laughing while drinking wine.

Often it’s those day-to-day moments that feel the most special. Board game nights, potluck dinners, or just chatting with friends are all meaningful, memorable occasions worthy of breaking out “holiday wines.” Sharing a drink with friends and loved ones is a wonderful way to encourage intimate conversation and connection.

When thinking about good wines to have on hand for a casual get-together, it can be helpful to choose easy crowd-pleasers. Cabernet sauvignon and chardonnay are the most popular wines in the country, and Chiswell has excellent vintages of both. Wine for chatting should be rich and pleasant to sip on its own, which means Chiswell’s 2021 Merlot is also an easy recommendation.

That said, good friends are there for you, not just to be impressed. If you have a wine you’re personally passionate about, they’ll be excited to try it with you!

Host Your Special Occasion at Chiswell

People enjoying private wine tasting at Chiswell

Even more fun than bringing wine to an event is bringing an event to the wine! Chiswell Farm & Winery is a delightful place to celebrate any occasion and is also open on many holidays. Look back on your special moments with fond memories of Blue Ridge views at a beautiful and historic estate.

For group gatherings, a private reserve tasting is a fun and intimate way to learn about wine and enjoy everything Chiswell has to offer. We also host seasonal events throughout the year, from live music to arts and crafts. And we may be biased, but who can imagine a more charming place to get married? No matter the occasion, we always enjoy helping you celebrate it in some small way.

Holiday Cooking with Apples

Apples pair beautifully with classic holiday flavors such as cinnamon, maple, and pecan. To prepare memorable, delicious holiday meals, use locally-grown apples and these recipes.

For recommendations on which apple varieties to use for cooking versus snacking, check out our apple profiles guide.


Breakfast

It’s Christmas morning and what’s that festive smell? Apples and cinnamon, of course!

Apple Danish Braid
Apple Cinnamon French Toast
Apple, Sausage & Smoked Cheddar Breakfast Casserole

Alternatively, our apple cider donuts are perfect for special occasions or breakfast any day. Freeze and reheat them for maximum freshness!

Chiles Warm Apple Cider Donut

Appetizers and Sides

Whether served with melty, buttery brie, pureed into soup, or tossed with a salad for extra crunch, apples lend a sweet touch to any side dish.

Baked Brie with Caramelized Apples & Spiced Praline Bacon
Apple-Butternut Squash Soup
Apple & Walnut Salad with Cider Vinaigrette


Dinner

You can’t go wrong with a traditional holiday ham with baked apples but for a new twist on the center of your holiday table, try these recipes.

Smoked Duck Breasts with Apple-brandy Caramel
Pork & Sauerkraut with Apples & Bacon
Baked Ham with Honey mustard & Apples


Dessert

It’s the holidays, go ahead and have dessert. From pies to cakes to cobblers, dessert is a dish best served with apples.

Glazed Puff Pastry Apple Roses
Caramel Apple Cake
Apple-Pomegranate Cobbler

Don’t feel like baking? Grab one of our fresh-baked apple pies. A classic for a reason!

Fresh-baked apple pie

Carter Mountain…sells pies that will make you want to slap someone on the butt! They are so delicious and flaky. The mix of apples they use creates the most interesting juxtaposition of sweet and tart. I highly recommend.

Jennifer J. via Nextdoor

Holiday Gift Guide

Shop local this holiday season with the Chiles Family Orchards holiday gift guide. Browse our Country Store or shop online to find the perfect gift for everyone on your list.

For the Friendly Competitors

Get ready for the ultimate battle of apples versus cider donuts! Duke it out on the solid wood checkerboard featuring Carter Mountain Orchard.

For the Young at Heart

It’s Pin the Tail on the Donkey, winter wonderland style! Stick the Carrot on the Snowman is fun game for all ages and easy to set up anywhere. And how cute is that snowman blindfold?

For the UVA Fan

Cozy up on one of these Kalalou picnic blankets, perfect for cheering on the University of Virginia.

For the Animal Lover

A fun, stylish piece for any children’s room, office, or dorm, these red stags by Cardboard Safari are easy to assemble and lightweight (which makes hanging a breeze). Bonus, the company is based in Charlottesville.

For the Family Hipster

A flattering color for anyone and delightfully warm, our branded beanies are the ideal winter headwear.

For the Fun Uncle

A 2020 collector’s item with a little bit of sass. These masked apple t-shirts are available in adult sizes with short sleeves in blue spruce and long sleeves in crimson.

For the Great British Bake Off Binger

A baking and serving vessel worthy of your home-baked creations! These pie plates are handcrafted in Virginia and oven, microwave, and dishwasher safe.

For the Apple Lover

It’s hard to go wrong with a jar of apple-y goodness. A versatile hostess gift, our Apple Butter and Honeycrisp Apple Sauce are delicious with breakfast, snacks, or dessert. There are so many tasty ways to cook with apple butter.

For the Sandwich Enthusiast

Enjoy our Blackberry Jelly in a classic PB&J or next level variation with honey wheat bread and almond butter. This sweet treat is also delicious with pastries or in thumbprint cookies.

For the Grill Master

Whether you’re firing up the grill for chicken, pulled pork, or ribs, slather on our Peach Barbecue Sauce to add a sweet, tangy flavor.

For the Health Nut

We might be famous for our indulgent apple cider donuts but we love salad too! (We’re farmers, after all.) This sweet, creamy Strawberry Poppyseed Dressing tastes like spring in a bottle and pairs well with spinach.

For the Hard-to-shop Fors

Gift cards are easy-peasy and what we all secretly want anyway.


Ready to knock out your holiday shopping?

Carter Mountain Holiday Festivities

Celebrate the most wonderful time of the year at Carter Mountain! Pancakes, pies, and holiday supplies—there’s something for everyone! Let the kids feast on cider and donuts while you shop the local crafts, specialty foods, ornaments, toys, and more. Take family photos with Santa and his sleigh, build a gingerbread house, and enjoy Charlottesville’s spectacular views. There are plenty of activities for all ages in the coming weeks, so be sure to check our events calendar to stay up-to-date.

Breakfast with Santa

This weekend, share a delicious pancake breakfast with Santa Claus himself at Breakfast with Santa. Enjoy family photos, Christmas crafts, and gingerbread house decorating all day with plenty of hot chocolate to go around. Santa will be around between 11AM and 3PM and crafts and shopping last all day.

Holiday on the Hill

December 10–11 and December 17–18, do your holiday shopping and take home a gingerbread house decorated by your family. Santa Claus will be available for photos on Saturday and the whole weekend will be filled with samples, sales, and Christmas spirit. Don’t forget that the Prince Michel Wine Shop and Bold Rock Hard Cider Cellar are always open—Christmas isn’t just about the kids, after all!

December Events at Carter Mountain

It’s the most wonderful time of the year! Join in the merrymaking at these upcoming festive holiday events.

Breakfast with Santa: December 5

Breakfast with Santa Claus at the Orchard in Charlottesville

What’s better than a homemade pancake breakfast with fresh fruit? A pancake breakfast with Santa! After breakfast, pose for a festive photo with Santa and his sleigh or write a letter to Saint Nick and drop it off for delivery in our special mailbox. Make a Christmas craft while sipping hot chocolate and singing along to Christmas carols—it doesn’t get merrier than that!

View event details

Check out Santa’s visit on November 28:
Video courtesy of NBC29 WVIR Charlottesville, VA

Holiday on the Hill: December 12, 13, 19, 20

Gingerbread house

For those who enjoy drinking warm alcoholic or non-alcoholic beverages with a beautiful backdrop, Holiday on the Hill is a great event to ring in the holidays. Do your holiday shopping, stock up on your favorite products for the winter, and enjoy samples, sales, and festive Christmas music.

Decorate a homemade gingerbread house at our gingerbread house workshops. The houses are ready-made; all you need to do is provide the decorative touches—and resist eating your house before it’s done!

We recommend registering in advance (call 434-977-1833) to ensure that participants have a spot at the gingerbread making table but walk-ins are welcome if space is available. Each day there will be four time slots at 10 a.m., 11 a.m., 1 p.m. and 3 p.m. Gingerbread house making and decorating is $25 per person.

Avoid the crowds at the mall and shop local.

“We love to see people come in and realize that it’s not as hectic here like it is at the mall or the big box stores, it’s a nice atmosphere here, with music playing, and we have hot cider,” Cynthia Chiles, Carter Mountain Orchard owner, said.