Holiday Shopping Spots to Visit This Season

You know that feeling when you stumble across the perfect gift while holiday shopping? That’s what makes this season so fun. We love pointing guests to festive markets and charming shops so their adventures stay joyful.

Consider this our shopping guide to help you enjoy the magic in Southwest Michigan. The festivities begin at the autumn artisan markets in Three Oaks and Valparaiso. So, let’s get started.

Arts & Crafts Festival

📆 Oct 18 | 9:30am – 4pm

The New Buffalo Service League hosts a large, old-school craft fair in the New Buffalo High School Gymnasium with over 90 vendors. There’s also a food and bake sale here, so get ready to taste Harbor Country while shopping. This is where the locals do their Christmas shopping!

Gather & Community Market

📆 Nov 8 | 9am – 1pm

Mingle with the locals at Gather & Community Market in New Troy, MI. Everyone shows up ready for the season. Local vendors sell handmade crafts, artwork, and goods you won’t find anywhere else.

Unique art pieces and jewelry
Handmade home goods
Local foods and snacks

This indoor market is held in New Troy, part of Harbor Country. New Troy is north of New Buffalo and about 15 minutes from Goldberry Woods. The Harbor Country events calendar provides specific details on dates. During early-season holiday shopping, this market makes finding something memorable and fun.

This market is held every second Saturday through Spring. If you miss one, another pops up the next month.

Shop Along Red Arrow Highway

Antique shopping in Harbor Country blends vintage discovery with handcrafted design. The variety of shops ensures every style has a place.

Harbert Antiques – timeless pieces with character and history
Hearthwoods Custom Furnishings – distinctive reclaimed wood furnishings
Lakeside Antiques – an eclectic mix of vintage decor and collectibles
Mazet Antiques – vintage furniture, decor, and collectibles in Three Oaks
Sawyer Antique Mall – an expansive selection of antiques, collectibles, and art
Sojourn – thoughtfully curated American handcrafts

Each shop offers something unique. Together, they make Red Arrow Highway a must for inspired shopping.

Three Oaks Autumn Artisan Market

📆 Nov 15 & 16 | 10am – 5pm
📆 Brunch served at 9am both days

This Three Oaks market is located within the Journeyman Distillery. You can sip craft cocktails at this market. You’ll wander through room after room of artisan booths. Local artisans fill the Three Oaks market with handmade treasures, seasonal treats, and creative gifts.

You’ll meet makers who pour their hearts into every piece. Some booths feature classic holiday décor. However, others highlight local foods that capture the season and tantalize your taste buds.

Round Barn Small Business Saturday Market

📆 Nov 29 | 12-5pm

After Thanksgiving, Saturdays become a celebration of local shopping traditions. Charming boutiques, art studios, and antique shops buzz with energy. This spot is where to shop for thoughtful and personal gifts.

Every Small Business Saturday Market purchase supports small businesses and strengthens the sense of community. Strolling downtown feels festive and fun, and you’ll enjoy chatting with shop owners who love their work.

Can’t-Miss Local Boutiques

Step into Flourish Books & Plants in New Buffalo, and curiosity immediately kicks in. It is the most delightful real bookstore and plant shop in New Buffalo. Bright bookshelves showcase new releases, timeless reads, and local gems. Plants add a lively touch, tucked among displays and perched beside stacks of books. You’ll also spot unique gifts, botanical art, and handy plant care tools.

Three Oaks has great shopping. Stop by Alapash, Poppy Hill Vintage, Vintage Goods, and Trilogy Antiques. Don’t miss Froelichs for great gourmet stocking stuffers.

New Buffalo has several great clothing boutiques, including The Love Spell Boutique and Glik’s. And if you’re looking for locally made artisan gifts, stop in at The Hidden Gem.

Holiday Market at Round Barn Winery & Estate

📆 Dec 13 | 12–5pm

December transforms the vineyard into a festive wonderland, and Round Barn Winery & Estate hosts its annual holiday market. You can browse through a curated selection of local artisans. Each offers a variety of gift ideas.

Shop seasonal decor, handcrafted goods, and unique gifts to check off your holiday gift list. Expect a warm, welcoming atmosphere and a beautiful winery backdrop to make your shopping feel extra special.

Sip & Shop for Stocking Stuffers

Shopping at our local wineries is a treat with many delicious sips to try. Local Pour offers carefully chosen wines and artisan goods perfect for holiday gifts. Hickory Creek Winery will charm you with its small-batch vintages and welcoming vibe.

Round Barn Winery elevates the variety with wines, craft beers, and spirits, making your gift-giving experience easier. Finally, Golden Muse Winery adds holiday flair with bold bottles and creative extras. These also double as conversation-worthy stocking stuffers.

With so many wineries to choose from, why wait? Taste first, then buy wine as stocking stuffers or holiday host gifts!

Seasonal fun beyond the shops

There’s more to Southwest Michigan than markets and boutiques. Bike trails wind through forests and dunes. Up for some adrenaline-pumping adventure? Riders enjoy crisp air, quiet paths, and winter scenery in every direction.

At Indiana Dunes National Park, nearly all trails stay open year-round. Only the Pinhook Bog Trail closes during the winter months. You still have miles of paths to enjoy, even in December.

Outings like these round out your trip. They give you even more reasons to love the area.

Your Holiday Getaway Awaits at Goldberry Woods

Every holiday trip deserves a cozy place to land. That’s where we come in. Our inn rests in Union Pier, surrounded by trails, orchards, and Lake Michigan charm.

You’ll love returning to warm rooms and peaceful grounds after a day of holiday shopping. Guests often head to our on-site trails for fresh air. Many also enjoy photographing winter birds, capturing snowy owls and cardinals in the quiet landscape.

This year, we will have a sustainable wrapping station. You can decorate all the great gifts you found during your holiday getaway.

What are you waiting for? Book a stay, and let Goldberry Woods be your hub for Southwest Michigan shopping adventures.