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  1. Home
  2. Sweetest Day

Sweetest Day Cookies

Sweetest Day is October 18, 2025

This Sweetest Day, send your sweetheart something extra special! Shop our unique and delicious Sweetest Day treats and cookies to make their day sweeter!

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Sending Lots of Love Party in a Box
Passport Eligible

Sending Lots of Love Party in a Box

available to ship now

Love Cookie Gift Tin
Passport Eligible

Love Cookie Gift Tin

available to ship now

Hug in Every Bite Gift Basket
Passport Eligible

Hug in Every Bite Gift Basket

available to ship october 06 2025

A Hug in Every Bite Cookie Card
FREE SHIPPING

A Hug in Every Bite Cookie Card

available to ship now

Rosé Wine and Cheryl's Cookies Box
Passport Eligible

Rosé Wine and Cheryl’s Cookies Box

Harry & David

available to ship now

Cupcake Cookie Dough Ice Cream and Cupcakessnipe
Passport Eligible

Cupcake Cookie Dough Ice Cream and Cupcakes

available to ship december 15 2025

Hug in Every Bite Cookie Gift Box
Passport Eligible

Hug in Every Bite Cookie Gift Box

available to ship now

You’re Incredible Party in a Box
Passport Eligible

You’re Incredible Party in a Box

available to ship now

LoveShackFancy Pretty in Pink Cookiessnipe
Passport Eligible

LoveShackFancy Pretty in Pink Cookies

available to ship now

Choose Your Own Bakery Assortmentsnipe
Passport Eligible

Choose Your Own Bakery Assortment

available to ship now

Our Best of Buttercream Cookies
Passport Eligible

Our Best of Buttercream Cookies

available to ship now

Buttercream Frosted Cut-out Cookie of the Month - Pay-as-you-go Subscription – 12 cookies
SAVE UP TO 42%
Passport Eligible

Buttercream Frosted Cut-out Cookie of the Month - Pay-as-you-go Subscription – 12 cookies

available to ship now

Barbie™ Buttercream-Frosted Sugar Cookiessnipe
Passport Eligible

Barbie™ Buttercream-Frosted Sugar Cookies

available to ship now

White Wine and Cheryl's Cookies Box
Passport Eligible

White Wine and Cheryl’s Cookies Box

Harry & David

available to ship now

Barbie™ Birthday Celebration Cookie Gift Boxsnipe
Passport Eligible

Barbie™ Birthday Celebration Cookie Gift Box

available to ship now

Cheryl’s Celebration Treats Gift Box
Passport Eligible

Cheryl’s Celebration Treats Gift Box

available to ship now

Two Dozen Red Roses, a Dozen Cheryl's® Cookies, and Wine
Passport Eligible

Two Dozen Red Roses, a Dozen Cheryl’s® Cookies, and Wine

Harry & David

available to ship november 03 2025

Barbie™ Long-Stem Buttercream Frosted Cookie Flowerssnipe
Passport Eligible

Barbie™ Long-Stem Buttercream Frosted Cookie Flowers

available to ship now

Cheryl's Celebration Gift Tower
Passport Eligible

Cheryl’s Celebration Gift Tower

available to ship now

LoveShackFancy Sugar Plum Cookiessnipe
Passport Eligible

LoveShackFancy Sugar Plum Cookies

available to ship now

Barbie™ Buttercream Frosted Sugar Cookie Gift Tinsnipe
Passport Eligible

Barbie™ Buttercream Frosted Sugar Cookie Gift Tin

available to ship now

Cupcake Cookie Dough Ice Cream and Cookiessnipe
Passport Eligible

Cupcake Cookie Dough Ice Cream and Cookies

available to ship now

Assorted Roses & Peruvian Lilies, Cheryl's® Cookies, and Wine
Passport Eligible

Assorted Roses & Peruvian Lilies, Cheryl’s® Cookies, and Wine

Harry & David

available to ship november 03 2025

Monster Chocolate Chip Cookiesnipe
Passport Eligible

Monster Chocolate Chip Cookie

available to ship now

Cheryl’s Celebration Cookie Pail
Passport Eligible

Cheryl’s Celebration Cookie Pail

available to ship now

Three Monster Chocolate Chip Cookiessnipe
Passport Eligible

Three Monster Chocolate Chip Cookies

available to ship now

Monster Chocolate Chip Cookies Frosting, and Sprinklessnipe
Passport Eligible

Monster Chocolate Chip Cookies Frosting, and Sprinkles

available to ship now

Red Wine and Cheryl's Cookies Box
Passport Eligible

Red Wine and Cheryl’s Cookies Box

Harry & David

available to ship now

LoveShackFancy Love in Bloom Cookiessnipe
Passport Eligible

LoveShackFancy Love in Bloom Cookies

available to ship now

Monster Chocolate Chip Cookie and Ice Creamsnipe
Passport Eligible

Monster Chocolate Chip Cookie and Ice Cream

available to ship now

Frank's RedHot® Cookie Flowerssnipe
Passport Eligible

Frank’s RedHot® Cookie Flowers

available to ship now

Blossoms & Wine™ - Red Roses and Wine
Passport Eligible

Blossoms & Wine™ - Red Roses and Wine

Harry & David

available to ship september 29 2025

Assorted Roses & Peruvian Lilies, Chocolate Truffles, and Wine
Passport Eligible

Assorted Roses & Peruvian Lilies, Chocolate Truffles, and Wine

Harry & David

available to ship now

Wedding Celebration Cookie Box
Passport Eligible

Wedding Celebration Cookie Box

available to ship now

Gourmet Drizzled Strawberries™, Chocolate Truffles, and Wine
Passport Eligible

Gourmet Drizzled Strawberries™, Chocolate Truffles, and Wine

Harry & David

available to ship now

Classic Cookie Assortment
FREE SHIPPING WITH CODE FRSHIP
Passport Eligible

Classic Cookie Assortment

available to ship now

Cheryl's Dessert Tray Gift Box - Medium - Enjoy
Passport Eligible

Cheryl’s Dessert Tray Gift Box - Medium - Enjoy

available to ship now

Signature Chocolate Truffles with Cheryl's® Cookies
Passport Eligible

Signature Chocolate Truffles with Cheryl’s® Cookies

Harry & David

available to ship now

Cheryl's® Cookies, Chocolate Truffles, and Wine
Passport Eligible

Cheryl’s® Cookies, Chocolate Truffles, and Wine

Harry & David

available to ship now

Cheryl's® Cookies, Gourmet Drizzled Strawberries™, and Wine
Passport Eligible

Cheryl’s® Cookies, Gourmet Drizzled Strawberries™, and Wine

Harry & David

available to ship november 03 2025

Enjoy Cookie Gift Box - 24 cookies
Passport Eligible

Enjoy Cookie Gift Box - 24 cookies

available to ship now

Cheryl’s Celebration Party in a Box
Passport Eligible

Cheryl’s Celebration Party in a Box

available to ship now

Cheryl’s Celebration Cookie Gift Box
Passport Eligible

Cheryl’s Celebration Cookie Gift Box

available to ship now

Sweet Popcorn Sampler Box
Passport Eligible

Sweet Popcorn Sampler Box

The Popcorn Factory

available to ship now

Simply Red 3 Flavor Popcorn Tins
Passport Eligible

Simply Red 3 Flavor Popcorn Tins

The Popcorn Factory

available to ship now

Snack Box
Passport Eligible

Snack Box

The Popcorn Factory

available to ship now

Tins With Pop® Love Hearts
Passport Eligible

Tins With Pop® Love Hearts

The Popcorn Factory

available to ship now

Tins With Pop® Sending Love Your Way 3 Flavor
Passport Eligible

Tins With Pop® Sending Love Your Way 3 Flavor

The Popcorn Factory

available to ship now

Tins With Pop® Double Red Hearts 3 Flavor
Passport Eligible

Tins With Pop® Double Red Hearts 3 Flavor

The Popcorn Factory

available to ship now

Tins With Pop® Retro Love 3 Flavor
Passport Eligible

Tins With Pop® Retro Love 3 Flavor

The Popcorn Factory

available to ship now

Tins With Pop® All You Need Is Love
Passport Eligible

Tins With Pop® All You Need Is Love

The Popcorn Factory

available to ship now

Cherry Blossom Pamper Her Spa Tower
Passport Eligible

Cherry Blossom Pamper Her Spa Tower

1-800-Baskets

available to ship now

Island Paradise Spa Tower
Passport Eligible

Island Paradise Spa Tower

1-800-Baskets

available to ship now

Denarii Lavender Spa Gift Basket
Passport Eligible

Denarii Lavender Spa Gift Basket

1-800-Baskets

available to ship now

Fruity Lovers 10 pc Macarons Asst
Passport Eligible

Fruity Lovers 10 pc Macarons Asst

1-800-Baskets

available to ship now

Chocolate Lovers 10 pc Macarons Asst
Passport Eligible

Chocolate Lovers 10 pc Macarons Asst

1-800-Baskets

available to ship now

Celebration 15 pc Macarons Asst
Passport Eligible

Celebration 15 pc Macarons Asst

1-800-Baskets

available to ship now

Signature Chocolate Truffles
Passport Eligible

Signature Chocolate Truffles

Harry & David

available to ship now

Chest of Chocolates
Passport Eligible

Chest of Chocolates

Harry & David

available to ship now

Harry's Best Chocolate Box
Passport Eligible

Harry’s Best Chocolate Box

Harry & David

available to ship now

Classic Tower of Chocolates® Gift
Passport Eligible

Classic Tower of Chocolates® Gift

Harry & David

available to ship now

Sweet Treats Wine Pairing Collection - Two Bottles
Passport Eligible

Sweet Treats Wine Pairing Collection - Two Bottles

Harry & David

available to ship now

Chocolates, Toffee, and Caramels
Passport Eligible

Chocolates, Toffee, and Caramels

Harry & David

available to ship now

Chocolate-Covered Cherries
Passport Eligible

Chocolate-Covered Cherries

Harry & David

available to ship october 13 2025

Moose Munch® Premium Popcorn Classic Tin
Passport Eligible

Moose Munch® Premium Popcorn Classic Tin

Harry & David

available to ship now

Belgian Chocolate Artisan Truffles
Passport Eligible

Belgian Chocolate Artisan Truffles

Harry & David

available to ship now

Gourmet Brownie Assortment
Passport Eligible

Gourmet Brownie Assortment

Harry & David

available to ship now

Deluxe Signature Cookie Basket
Passport Eligible

Deluxe Signature Cookie Basket

Harry & David

available to ship now

Cheesecake Party Wheel
Passport Eligible

Cheesecake Party Wheel

Harry & David

available to ship now

Happy Bug Chocolate-Covered Apples and Cake Pops
Passport Eligible

Happy Bug Chocolate-Covered Apples and Cake Pops

Harry & David

available to ship now

Fruit and Nut Belgian Chocolate Bark Assortment
Passport Eligible

Fruit and Nut Belgian Chocolate Bark Assortment

Harry & David

available to ship now

Scharffen Berger® Holiday Chocolatier's Collection - 20 Piece
Passport Eligible

Scharffen Berger® Holiday Chocolatier’s Collection - 20 Piece

Harry & David

available to ship october 27 2025

Scharffen Berger® Chocolatier's Collection - 36 Piece
Passport Eligible

Scharffen Berger® Chocolatier’s Collection - 36 Piece

Harry & David

available to ship now

Bakery Tray - Signature
Passport Eligible

Bakery Tray - Signature

Harry & David

available to ship now

Linzer Tart Cookies
Passport Eligible

Linzer Tart Cookies

Wolferman's

available to ship now

Classic Cinnamon Rolls
Passport Eligible

Classic Cinnamon Rolls

Wolferman's

available to ship now

Deluxe Berry Breakfast Box
Passport Eligible

Deluxe Berry Breakfast Box

Wolferman's

available to ship now

Mix & Match Bakery Gift - Pick 4
Passport Eligible

Mix & Match Bakery Gift - Pick 4

Wolferman's

available to ship now

Mix & Match Bakery Gift - Pick 6
Passport Eligible

Mix & Match Bakery Gift - Pick 6

Wolferman's

available to ship now

Mix & Match Bakery Gift - Pick 12
Passport Eligible

Mix & Match Bakery Gift - Pick 12

Wolferman's

available to ship now

Blooming Love™ Premium Red Roses
Passport Eligible

Blooming Love™ Premium Red Roses

1-800-Flowers

Fields of Europe® Romance Bouquet
Passport Eligible

Fields of Europe® Romance Bouquet

1-800-Flowers

One of a Kind Bouquet | Love & Romance
Passport Eligible

One of a Kind Bouquet | Love & Romance

1-800-Flowers

Two Dozen Red Roses
Passport Eligible

Two Dozen Red Roses

1-800-Flowers

Magnificent Pink Rose & Lily Bouquet
Passport Eligible

Magnificent Pink Rose & Lily Bouquet

1-800-Flowers

Sweet Succulent Heart Garden
Passport Eligible

Sweet Succulent Heart Garden

1-800-Flowers

Sweet Blooms Calla Lily
Passport Eligible

Sweet Blooms Calla Lily

1-800-Flowers

Lovable Pup Rose Plant
Passport Eligible

Lovable Pup Rose Plant

1-800-Flowers

"You Are Flamazing" Jumbo Plush
Passport Eligible

“You Are Flamazing” Jumbo Plush

1-800-Flowers

Sweet & Delicious™
Passport Eligible

Sweet & Delicious™

Fruit Bouquets

Delightful Daisy Treat™
Passport Eligible

Delightful Daisy Treat™

Fruit Bouquets

Gourmet Drizzled Strawberries™
Passport Eligible

Gourmet Drizzled Strawberries™

Shari's Berries

Signature Bundt Cake Assortment™ with Gourmet Drizzled Strawberries
Passport Eligible

Signature Bundt Cake Assortment™ with Gourmet Drizzled Strawberries

Shari's Berries

Classic Cheesecake Bites™ With Gourmet Drizzled Strawberries™
Passport Eligible

Classic Cheesecake Bites™ With Gourmet Drizzled Strawberries™

Shari's Berries

Love You Bloom Box with Cake

Love You Bloom Box with Cake

Created By: Send A Cake

Love Explosion Cake Gift Box

Love Explosion Cake Gift Box

Created By: Send A Cake

Red Rose Spa Gift Set
Passport Eligible

Red Rose Spa Gift Set

Small Dried Flower Bouquet
Passport Eligible

Small Dried Flower Bouquet

ICE CREAM CANDLE
Passport Eligible

ICE CREAM CANDLE

Classic Comfort Personalized Luxury Fleece Robes
PASSPORT BONUS POINTS
Passport Eligible

Classic Comfort Personalized Luxury Fleece Robes

Personalization Mall

LOVE Personalized Photo Shelf Blocks - Set of 4
Passport Eligible

LOVE Personalized Photo Shelf Blocks - Set of 4

Personalization Mall

Close To Her Heart Personalized Blanket
PASSPORT BONUS POINTS
Passport Eligible

Close To Her Heart Personalized Blanket

Personalization Mall

Your Love Letter Personalized Keepsake
Passport Eligible

Your Love Letter Personalized Keepsake

Personalization Mall

Timeless Love Personalized Sand-Filled Hourglass
Passport Eligible

Timeless Love Personalized Sand-Filled Hourglass

Personalization Mall

Love Connection Personalized Mini Heart Photo Puzzle
Passport Eligible

Love Connection Personalized Mini Heart Photo Puzzle

Personalization Mall

Fortunate Love Personalized Fortune Cookie
Passport Eligible

Fortunate Love Personalized Fortune Cookie

Personalization Mall

Orrefors Engraved Crystal Romantic Heart Bud Vase
Passport Eligible

Orrefors Engraved Crystal Romantic Heart Bud Vase

Personalization Mall

Pizza Expressions Personalized 3pc Pizza Board Gift Set
Passport Eligible

Pizza Expressions Personalized 3pc Pizza Board Gift Set

Personalization Mall

I Cerealsly Love You Personalized 14 oz. Romantic Cereal Bowl
Passport Eligible

I Cerealsly Love You Personalized 14 oz. Romantic Cereal Bowl

Personalization Mall

You're All I Need Personalized Keepsake
Passport Eligible

You’re All I Need Personalized Keepsake

Personalization Mall

For Her Engraved Keepsake Rose
Passport Eligible

For Her Engraved Keepsake Rose

Personalization Mall

3 Count Oscar Mayer Bacon Cheddar Popcorn Bags
Passport Eligible

3 Count Oscar Mayer Bacon Cheddar Popcorn Bags

The Popcorn Factory

available to ship now

3 Count Kraft Mac & Cheese Popcorn Bags
Passport Eligible

3 Count Kraft Mac & Cheese Popcorn Bags

The Popcorn Factory

available to ship now

Engraved Scroll Heart Keepsake Box
Passport Eligible

Engraved Scroll Heart Keepsake Box

Things Remembered

Engraved Musical Floral Photo Snow Globe
Passport Eligible

Engraved Musical Floral Photo Snow Globe

Things Remembered

Engraved Monogram Vera Wang Crystal Leaf Vase
Passport Eligible

Engraved Monogram Vera Wang Crystal Leaf Vase

Things Remembered

Orrefors Engraved Anniversary Crystal Heart Bud Vase
Passport Eligible

Orrefors Engraved Anniversary Crystal Heart Bud Vase

Things Remembered

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Sweetest Day Gifts

This Sweetest Day, make your loved one feel truly special with a gift that’s as sweet as they are! At Cheryl's, we specialize in creating unique and delicious Sweetest Day cookie gifts that are sure to delight. Our freshly baked cookies are crafted with care, featuring our famous buttercream frosting and a variety of delightful flavors. Whether you're sending a dessert assortment or a festive cookie gift basket, our Sweetest Day gifts are the perfect way to show you care. Don't wait, shop now and schedule your delivery for Sweetest Day on October 18th to ensure a sweet surprise awaits your sweetheart.

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