Small-town warmth. Local flavor. Sweet-tooth legend. Whitman, Massachusetts may only span 6.97 square miles, but it’s absolutely packed with personality—and plenty of spots worth a Saturday ramble.
Whether you’re a South Shore local looking to rediscover a familiar town, a Greater Boston day-tripper craving handcrafted ice cream and indie shopping, or a new homeowner scouting weekend fun (hi, friends of The Jenkins Group! 👋), this guide will help you plan an easy, memory-making outing in Whitman.
Quick-Glance Whitman Highlights
Famous For: Being the birthplace of the original Toll House Chocolate Chip Cookie (yes, that cookie!).
Vibe: Friendly, quietly historic, with a surprising number of small businesses tucked into downtown storefronts and along Bedford, Washington, and South Ave.
Perfect For: Family afternoons in the park, grab-and-go farm treats, casual craft beer tastings, vintage treasure hunting, and supporting local makers.
Table of Contents
-
Shop Local: Boutiques, Gifts & One-of-a-Kind Finds
-
Hornstra Farm Store & (Formerly Peaceful Meadows) Dairy Bar
-
Gold Star Treasures Antique & Vintage Mall
-
Abbey London Boutique (Local Style)
-
Designs by Devine (Gifts & Decor)
-
Little Comfort General Store (Everyday Local Charm)
-
Monument Print Co. (Custom Local Gear)
-
-
Explore Whitman: Parks, Flavor & Local Hangouts
-
Whitman Town Park (Olmsted-Designed Gem!)
-
Community Pool & Playground
-
Old Colony Brewing Taproom
-
Toll House Cookie History Stop
-
Seasonal Markets & Pop-Up Vendor Days
-
Make It a Day Trip: Sample Itinerary
Total Time: 4–6 hours depending on how often you linger (and how many scoops of ice cream you order 😋).
Morning (10:00 AM) – Arrive downtown. Start with a quick browse at Abbey London Boutique or Designs by Devine for gifts or local flair.
Late Morning (11:00 AM) – Head to Gold Star Treasures Antique & Vintage Mall. Give yourself at least 45 minutes—there are multiple vendors and lots of “wait, come look at this!” moments.
Lunch-ish Treat (12:15 PM) – Swing by Hornstra’s Farm Store & Dairy Bar (at the longtime Peaceful Meadows site) for dairy-fresh ice cream, pints to go, and local provisions.
Afternoon (1:00 PM – 3:00 PM) – Relax at Whitman Town Park: stroll the loop path, let kids loose on the playground, or bring a picnic under the trees. In-season? Cool off at the Town Pool.
Late Afternoon (3:30 PM) – Grab a flight at Old Colony Brewing before you head home. Rotate designated drivers or pick up cans to go.
Bonus: If you’re touring homes nearby (call The Jenkins Group—we’ll line it up!), we can build showings around your Whitman adventure.
Shop Local: Boutiques, Gifts & One-of-a-Kind Finds
Whitman’s retail scene is small but mighty—heavy on local ownership, creativity, and community spirit. Here are our favorite stops (grouped by vibe so you can mix & match your outing).
Hornstra Farm Store & Dairy Bar (at the beloved former Peaceful Meadows location)
Address: 60 Bedford St., Whitman, MA 02382
What You’ll Find: Handcrafted ice cream, farm-fresh dairy, seasonal flavors, pints & quarts to go, and a sweet dose of South Shore nostalgia.
Why Go: The site has long been iconic in town thanks to the Peaceful Meadows dairy legacy. Under Hornstra Farms’ care, you still get that farm-stand feel plus scratch-made ice cream scoops that make any Whitman visit a win.
Pro Tip: If you’re freezer-stocking, grab extra—Hornstra’s rich base and rotating flavors disappear fast at parties. Bring a cooler if you’re touring homes afterward.
Gold Star Treasures Antique & Vintage Mall
Address: 356A South Ave., Whitman, MA
What You’ll Find: Multi-vendor antique booths, vintage décor, furniture refresh candidates, collectible oddities, retro signage, and seasonal treasure hunts (holiday décor jackpot!).
Why Go: It’s the kind of place where you walk in looking for “maybe a lamp” and leave with a 1960s Coke crate, a framed map, and a conversation piece for your mantle. Perfect for new homeowners staging, styling, or personalizing a space on a budget.
Allow: Minimum 45 minutes; longer if you love to dig.
Abbey London Boutique (Local Style & Accessories)
Great For: Women’s clothing, accessories, seasonal wardrobes, and boutique giftables.
Why Go: Support a locally-owned fashion boutique without trekking into the city. Ideal pre-dinner stop if you’re heading out on the South Shore.
Style Tip: Ask about new-arrival racks—boutique owners often bring in ultra-limited runs.
Designs by Devine (Gifts, Seasonal Decor & Local Love)
Vibe: Gift shop meets small-scale lifestyle boutique. Think hostess gifts, décor accents, coastal-New England touches, and holiday switch-outs.
Why Go: Easy one-stop grab when you need a closing gift, thank-you basket add-on, or front-door seasonal refresh.
Little Comfort General Store
Address: 50 Washington St., Whitman, MA
What You’ll Find: Everyday staples, snacks, and the heart-of-town general store charm that reminds you you’re in New England.
Why Go: Quick grab spot for drinks before the park, picnic snacks, or a “we forgot the sunscreen” rescue.
Monument Print Co. (Custom Gear, Signs & Merch)
Good For: Local swag, branded apparel, signage, event merch, team gear, and custom print projects.
Why Go: If you’re planning a community event, school fundraiser, or want hyper-local closing gifts branded with a neighborhood name—this is your print partner.
Explore Whitman: Parks, Flavor & Local Hangouts
Whitman Town Park (Historic & Designed by the Olmsted Brothers)
Location: Surrounded by Maple St., Park Ave., Whitman Ave., and Hayden Ave. (Main entrance near 141 Whitman Ave.)
Size: ~14 acres.
Why It’s Special: The park’s landscape plan traces back to the famed Olmsted Brothers (sons of Frederick Law Olmsted, designer of Boston’s Emerald Necklace and NYC’s Central Park). Rolling lawns, mature shade trees, a central pond fountain, walking paths, and civic memorials give it that classic New England common-meets-park feel.
What to Do:
-
Walk the ~0.45-mile perimeter path.
-
Let kids hit the updated playground (separate areas by age).
-
Pack a picnic—there are benches & tables.
-
In winter, local families sled the park’s gentle hills.
-
History buffs: check out the Civil War Soldiers & Sailors Monument (dedicated 1908) and other memorials.
Town Pool & Seasonal Recreation
If you’re visiting in summer, Whitman’s seasonal Town Pool (located in/adjacent to the park complex) is a family favorite. Day passes are typically available; residents of Whitman and neighboring Hanson get priority access, so bring ID. Hours vary by season—check before you go (we’re happy to help you confirm!).
Old Colony Brewing Taproom
Address: 599 Washington St., Whitman, MA 02382
Style: Small, community-rooted craft brewery with rotating taps.
Expect: IPAs, seasonal brews (keep an eye out for Whitman Wheat, Farmhouse, Pumpkin Ale, or fun small-batch experiments), and a relaxed taproom where locals actually talk to each other.
Hours Snapshot: Typically open Friday evenings and weekend afternoons/evenings; hours shift seasonally, so check before rolling in with a crew.
Bring: Friends, dogs (call ahead to confirm current policy), and your curiosity—try a flight and take home Crowlers or 4-packs.
Toll House Cookie History Stop
Whitman’s most famous claim to culinary fame? The original Toll House Cookie, created in the 1930s by Ruth Wakefield at the Toll House Inn right here in town. While the original inn no longer operates as it once did, the story lives on in baking lore—and every chocolate chip cookie you’ve ever loved. If you’re touring with kids, tell them this is the town that changed dessert forever. (Bonus activity: bake Toll House cookies at home after your Whitman day!)
Seasonal Markets & Pop-Up Vendor Days
From farm pop-ups and church craft fairs to emerging community farmers markets, Whitman and nearby South Shore towns love a vendor tent. Keep an eye out in spring and fall for maker markets (often hosted at local farms, schools, or community fields). If you’d like a current list, reach out—we can round up this season’s dates.
Kid-Friendly Stops
-
Whitman Town Park Playground: Safe surfacing, equipment for multiple ages, benches for grown-ups.
-
Ice Cream at Hornstra’s Dairy Bar: Guaranteed smiles.
-
Seasonal Pool Splash Time: Great reward after errands or open houses.
-
Treasure Hunt at Gold Star Treasures: Give each kid $5 to find “something weird & wonderful.”
Rainy-Day Backups
Whitman is small, so for a soggy afternoon consider pairing your visit with nearby South Shore indoor options: bowling in neighboring towns, indoor play spaces in Hanover or Rockland, or a brewery-to-bakery crawl (OCB + local cafes). We can suggest a weather-proof route based on who’s in your group.
Local Events to Watch
Whitman and greater Plymouth County host rotating seasonal happenings—outdoor concerts in the park, community days, trunk-or-treat events, vendor fairs, and heritage/history programs (the Toll House story always comes back around!). If you’d like, we’ll add you to The Jenkins Group newsletters so you never miss one.
Map It & Parking Tips
-
Downtown Cluster: Abbey London Boutique, Designs by Devine, Monument Print Co., and general stores are short drives from each other—street or small-lot parking typical.
-
Gold Star Treasures: On South Ave.; look for onsite or street-side parking—weekends can get busy.
-
Hornstra’s Farm Store / Dairy Bar: Bedford St.—expect a classic farm-stand style lot; summer evenings draw lines.
-
Whitman Town Park: Multiple periphery streets; obey posted rules, especially during events or pool season.
-
Old Colony Brewing: Washington St.—strip-style/lot parking; always double-check posted hours before you roll in.
Make It a Real Estate Adventure
Thinking about moving to (or investing in) Whitman? Combine your day of exploring with a showing tour of available homes, multi-families, or investment properties in Whitman and nearby South Shore communities. We’ll build a route that includes:
-
Ice cream stop (non-negotiable 🍦)
-
Park walk to get a sense of the neighborhood
-
Drive-bys of schools & commuter routes
-
Local shopping & service introductions (because lifestyle matters!)
Ready to plan it? Reach out to The Jenkins Group—we’ll tailor the outing to your timeline, budget, and goals.
Final Scoop (Pun Intended 😄)
Whitman isn’t flashy—but that’s its superpower. Here, you get friendly faces, history underfoot, and locally-owned businesses that remember your name after your second visit. Come for the ice cream, stay for the park stroll, and leave with a trunk full of vintage finds and a new favorite brewery.
Let us know when you’re coming—The Jenkins Group would love to help you explore Whitman like a local!
Written with love (and probably a chocolate chip cookie in hand) -The Jenkins Group.
