Rhinebeck
First, a quick overview: Downtown is T-shaped—so start off on Market (there are two parking lots, next to and across from CVS) and head toward Montgomery. After your day of retail therapy, you can catch a performance The CENTER for Performing Arts and the Fisher Center at Bard College (Annandale), or a movie at Upstate Films’ Starr Cinema on Montgomery Street. The CENTER frequently puts on big musicals with local talent, such as “Little Shop of Horrors.” On Saturday mornings, check out family programming like puppet shows or birds of prey lectures.
Market Street: A not-so-secret fact: Paul Rudd, Jeffrey Dean Morgan, and Hilarie Burton Morgan co-own Samuel’s Sweet Shop, a beloved candy store (which is celebrating its 30th birthday) selling artisanal bonbons, sweets, and imported treats that are hard to find elsewhere. Local real estate pros Jon and Delyse Berry’s Upstate Down Shoppe features the couple’s favorite home goods, from bath products to decorative statement pieces. Find the perfect gift for the kids at Land of Oz, a toy store with imaginative arts and crafts, puzzles, stuffed animals, and games. Periwinkles has a little bit of everything: beaded jewelry, bath bombs, handmade soaps, knitted socks, and even a case dedicated to dog treats. Collectors will love Megabrain Comics, an emporium of new and vintage comic books and vinyl. Near the intersection, stop by Rhinebeck Mercantile—a boutique with apparel and accessories, games to play with the family, totes, and more—before turning right for the next batch of shops.
Lunch Break
- A falafel sandwich with all the sauces at beloved Aba’s Falafel. 54 East Market
- Ocra chicken dosa (a weekend brunch special) at Cinnamon. 51 East Market
Montgomery Street: Walk a block north to the Montgomery Row Building, where you’ll find Oblong Books and Hammertown. Oblong is a beloved bookshop with a vast collection of literature, including signed editions and a dedicated Hudson Valley section. You might find your next favorite piece of furniture at Hammertown, which offers everything from sofas and dining chairs to rugs and tableware. Across the street is Paper Trail which specializes in stationery and paper goods (such as planners, calendars, and greeting cards), along with jewelry, eyewear, and fashion accessories. Right next door is StarryBird Kids, a chic children’s boutique stocked with footwear and rain gear, seasonal clothing, school supplies, plus maternity and nursing items. As you approach the corner once again, stop by Irwin Garden—a nursery and home goods shop with gorgeous dried flower bouquets, handmade ceramics, and a natural apothecary.
Fashion Finds
- Cabin Fever Outfitters (outdoor wear), 6406 Montgomery
- Darryl’s, 18A East Market
- Merriweather’s, 51 East Market
- Pegasus Footwear (shoes), 3 East Market
- Willow Wood, 38 East Market
- Winter Sun & Summer Moon, 10–14 East Market
- Workers & Dreamers, 6404 Montgomery
- Zephyr, 28 East Market
Hudson
Once a whaling hub, Hudson is now lined with high-end boutiques, home décor stores, vintage shops, and more. Here, you can spend an entire day just shopping. Most of the businesses are along (or just off) Warren Street, a mile-long stretch that runs from the intersection of Route 9 down to the riverfront.
Hudson is well-known for is its abundance of antique shops. A few to stop in: Cooper & Company, A Collector’s Eye, Arenskjold Antiques, Art and More, and Red Chair on Warren. You can also spend a day browsing the 40,000-square-foot Antique Warehouse on Front Street.
200-300 Blocks: Starting from the bottom of Warren, you’ll find shops scattered throughout architecturally diverse storefronts. For quirky greeting cards, notebooks, planners, and other stationery, step into The Social Type. Botanical apothecary Florent carries a line of natural skincare products and perfumes. A curated mix of furniture, clothing, linens, rugs, and more await at Lili and Loo. A popular design firm sets up shop at Foley & Cox Home, which offers vintage furnishings, custom-designed outdoor furniture and upholstery, and contemporary art. More décor selected by high-end interior designers is at Hudson Home.
400-500 Blocks: This is probably the busiest section of Warren. Duck into more home stores like Minna, which has bedding, rugs, and other ethically made textile goods. Finch Hudson stocks both vintage and modern furniture, plus apparel, art, and accessories. If you want to pick up something for your furry friend, pet goods like cute sweaters, plush toys, and fashionable beds and bowls can be bought at Love Thy Beast. You can get books, art supplies, and sip a craft beer at The Spotty Dog Books & Ale. Beautiful fabrics are designed in-house and turned into curtains, pillowcases, table runners, and more at Les Indiennes. Visit The Quiet Botanist to add a pop of color to your home with a fresh bouquet or dried floral arrangement. Fig & Bella and shoe store Intentionally Blank both carry wardrobe accessories; and don’t miss Upstate Rug Supply, which displays a wide collection of antique carpets that have been sourced, professionally washed, and preserved by the owner.
Lunch Break
- Soup du jour (such as carrot ginger or potato and leek) at Le Perche. 230 Warren
- Signature pork schnitzel at Wunderbar Bistro. 744 Warren
600-700 Blocks: End your day on upper Warren. Find vintage and custom jewelry pieces at gem store The Moonstoned. Homewares like tinted glass carafes, wooden cutting boards, and even modern lighting fixtures can all be purchased at Gestalt Haus. Grab a great gift for anyone at Valley Variety, home to bold tissue box covers, unique puzzles and games, Baggu bags, and stylish wall clocks. And, while Poured Candle Bar may be known for their DIY custom candle experiences, you can also browse their line of signature fragrances and scents (we love the Passage candle).
Fashion Finds
- Manifest Boutique, 356 Warren
- Hudson Clothier (American-made), 443 Warren
- Westerlind (outdoor clothes), 419 Warren
- Look Apparel and Accessories (vintage),401 Warren
- Behida Dolic Millinery (hats and womenswear), 610 ½ Warren
Kingston
A sprawling Ulster County city, Kingston’s shops are spread among three distinct districts—so be prepared to hop in and out of your car to make the most of your day. Start uptown in the historic Stockade and make your way down through Midtown to the Rondout, Kingston’s waterfront district. And don’t worry about parking—there are plenty of metered lots and street spots.
Stockade: Many of Uptown’s shops are housed in old storefronts that date back to the Revolution. Find your next read (and get a specialty coffee or craft beer) at Rough Draft Bar & Books. Flora Beauty has an array of small-batch home goods, from ceramics to art prints, and natural beauty and wellness products. The eclectic Magic Hill Mercantile is stocked with mid-century furniture and colorful original art designs that adorn coasters, pillows, scarves, dresses, and more. A hub for décor, Exit Nineteen carries everything from elegant tableware and throw pillows to whimsical faux wooden birdhouses and portraits of aristocratic animals. If you want to up your kitchen game, a stop into Bluecashew Kitchen Homestead is a must; the shop carries cookbooks as well as chic cookware, utensils, and high-end oils and vinegars. And, for a wide selection of gifts like scented candles, themed stationery, costume jewelry, air plants, and wall hangings, visit Newt.
Lunch Break
- Egg dishes (like a spicy southwestern wrap and the Mediterranean-inspired Jimmy pesto) at Sissy’s. 324 Wall
- Elevated deli sandwiches at the Rondout’s Rosie General. 39 Broadway
Midtown Pitstop
On your way to the Rondout, make sure to check out the 10,000-square-foot Red Owl Collective, an antique, vintage, and design store filled with apparel and furniture.
Rondout: After turning onto lower Broadway, park near the top of the hill and stroll down. The first store you’ll pass is Milne Antiques, a showroom with rugs, lighting fixtures, furniture pieces, and wall hangings. For more vintage pieces, stop into Spruce Design & Décor. In Chicory Naturalist, you’ll find nature-themed books, pins, games, and outdoor gear like binoculars for all ages. Fine jewelry purveyor Facets of Earth has custom designs on display; and Clove & Creek is filled with homewares, like blankets and décor, and apothecary products (they have a second location in Hudson). Before heading home, buy some vino from indie bottle shop Kingston Wine Co.
Fashion Finds
- Next Boutique, 17 West Strand
- Theresa & Company, 303 Wall
- Karina, 329 Wall
- Rewind (vintage), 612 Broadway
- At Land, 534 Broadway
- Lovefield Vintage, 37 North Front
- Hamilton & Adams, 32 John
Beacon
Brimming with chic, fun shops, Beacon’s Main Street is over a mile long (so now is not the time to break in those new boots). Start your spree on the west end of Main, by Bank Square Coffeehouse. There are free parking lots throughout the city (if you can’t find street parking), and this side of Main is closest to the Metro-North Beacon Station.
West Main: As you make your way up the block, you’ll come across your first batch of stores. If you love kitchenware, you’ll find practically everything you need at Utensil, from steel saucier pans to Stasher bags to bar glasses, and Stella’s, for international and unique pantry goods, a variety of cookbooks, and zero-proof drinks. Hunca Munca’s has a curated selection of whimsical gifts for children of all ages. Find your next favorite piece of jewelry (like open-cuff bracelets, drop earrings, and bold necklaces) and calming candles or diffusers, plus greeting cards and paper goods, at Lewis & Pine. If you’re outdoorsy, Mountain Tops Outfitters—and the Last Outpost Store, which is seven blocks east—carry name-brand and artisan hiking gear, footwear, apparel, and accessories. Near the Main Street Park, check out Witch Hazel, an eco-friendly apothecary and beauty store. Across the street is Zakka Joy, a colorful hub for kids and adults alike for stationery and pens to imported Japanese toys and goods to trendy home goods. (Their zany sock wall is fantastic.) Your last two stops before lunch should be Flora Good Times, a plant shop with unique flora plus pottery, and Little King, a stunning home goods store that blends Scandinavian and Asian flair into its kitchen and dining products, pantry items and accessories. For the next couple of blocks—from Walnut Street to Teller Avenue—there is a bit of a lull, so that might be the best time to eat.
Lunch Break
- Weekend brunch (the crispy brunch wrap is a favorite) at Homespun Foods. 232 Main
- Himalayan-style spinach and cheese or chicken dumplings at Momo Valley. 455 Main
East Main: Once you’re refueled head to Sybil, a quaint shop with a collection of artisanal home goods (embroidered pillows and throw blankets), kitchenware, and bath products. The owner recently opened Sibling (504 Main), a children’s boutique with cute toys and books. At the bend in the road, step into Raven Rose for botanical and wellness gifts and floral arrangements, and Solstad House, a small general store with creative books, Beacon-inspired merch, cocktail mixers, and more. Berte is a home and lifestyle shop with ceramics and kitchenware crafted by local makers, herbal and skincare lines, and jewelry. Stanza Books is Beacon’s latest shop offering new releases and classics.
Fashion Finds
- Blackbird Attic (vintage), 442 Main
- Colorant, 146 Main
- Darryl’s, 155 Main
- House of Maxx, 206 Main
- Hyperbole, 484 Main
- KAIGHT, 512 Main
- NFP: Beacon, 457 Main
- Wanderlux, 475 Main
Woodstock
Since the ‘60s, Woodstock has been synonymous with creativity and the arts. This reputation extends into the town’s shopping scene, where many stores specialize in goods from local makers. Two streets host most of the businesses: Tinker and Mill Hill Road. You can park in a public lot on Rock City Road, a short walk from where they meet. End your day by viewing local works at the Woodstock Artists Association & Museum, or catch a concert at The Colony, Bearsville Theater, or Levon Helm Studios.
Mill Hill: From the intersection in the middle of town, head east. Candlestock is worth a stop for its scented and decorative candles, plus hand-dipped drip candles. Casa Ziki carries a collection of unique, design-forward home décor, accessories, and gifts. You’ll find sustainable stationery at Lovewild Design, plus low-waste bath and body products like bath salts, shower steamers, and vegan lotion bars that are crafted in their Brooklyn flagship location.
Lunch Break
- Soups, salads, and sandwiches at Bread Alone. 22 Mill Hill
- All-day breakfast (try the eggs Benedict) at Oriole 9. 17 Tinker
Tinker: Continue your day at cozy bookstore The Golden Notebook; you’ll find classics and the newest releases on the first floor (plus books they independently publish), and upstairs is filled with children’s titles. Shop Little House carries art, stationery, tableware, and home goods like fine wool blankets. Take a brief detour down Tannery Brook Road to visit Timbuktu, a jewelry and accessories gift shop. (While you’re there, break for a minute at roadside Woodstock Waterfall Park for a pretty view of the brook.) Back on Tinker, find whimsical prints, retro-looking throw pillows, disco ball planters, and more at Maverick Road. And for locally made vases, tableware, textiles, and other décor, visit Beck Home + Goods.
Fashion Finds
- Changes (menswear), 19 Tinker
- Birchtree (eco-friendly), 6 Tannery Brook
- idPearl (indie designers), 97 Tinker
- Pegasus Footwear (shoes), 10 Mill Hill
Cold Spring
Although this sweet Putnam village has one of the shorter shopping streets on our list, that doesn’t mean it’s any less enjoyable. Spend the morning perusing stores, break for lunch, then walk through the pedestrian tunnel (by the train tracks) for Hudson River views at Dockside Park. Afterward, hop in the car and head to Magazzino Italian Art. The museum has a few fantastic exhibits, including “Carlo Scarpa: Timeless Masterpieces,” where you can view 56 pieces of Murano glassworks by the famous architect. If it’s a nice day, check out a nearby hiking trail such as Little Stony Point or the Cornish Estate, both off Route 9.
From the Top: Start at Chestnut and Main and check out Supplies for Creative Living, where there’s a plethora of arts and writing materials from watercolor sets and journaling kits to sketchbooks and washi tapes. If you’re a foodie, pop into Cold Spring Cheese Shop for international and local fromage and provisions, and Flowercup Wine for curated bottles of vino. Mundane is a make-your-own candle workshop but sells signature scents and blends in diffusers and candles, plus stationery and candle accessories. Split Rock Books has a great collection of new releases and classics.
Lunch Break
- Croque monsieurs and Alsacienne onion soup at brasserie Le Bouchon. 76 Main
- Cacio e pepe and calamari at Cathryn’s Tuscan Grill. 91 Main
All the greeting cards you could ever want plus cute gifts (games, prints, and kid’s toys) are on display at Pink Olive. Inside Cold Spring General Store you’ll find books, candles, and bath products; chic apparel is on the second floor; and the back is dedicated to local provisions like beer, jams and spreads, and snacks. Poor George recently moved their vibrant selections—including both vintage and new clothing, jewelry, and home décor—a few doors down (from 60 Main) into a larger space at the corner of Main and Stone streets. Cold Spring Apothecary and Wellness House is ideal for all your beauty and skincare needs, from their best-selling amber hand cream to vanilla oak body lotion.
Fashion Finds
- Cold Starts, 64 Main
- DamnAged Vintage (vintage), 109 Main
- Love Letter (lingerie), 153 Main
- Lucestella Studio (sandals), 165 Main
- Old Souls, 63 Main
- Paulette, 114 Main
Related: What to Eat at The Academy Food Hall in Poughkeepsie
