Sip Your Way Around Cape Cod: Where to Find Great Wine

Cape Cod might be best known for its beaches, lobster rolls, and clam chowder, but we wouldn't have put down roots here if there weren’t also a few spots to enjoy a great glass of wine. Depending on what you're in the mood for, you can spend an afternoon among the grapevines, discover a bottle you’ve never tried at a local wine shop, or settle in for dinner with a wine pairing chosen to complement every course.

Here are a few places we'd recommend adding to your plans when staying at our Cape Cod bed and breakfast.

11 Shore Road, North Truro

If you're planning a day in Provincetown or just want to explore more of the Cape, make room in your plans for Truro Vineyards. It’s one of the best-known vineyards in Massachusetts, and with a historic farmhouse, rows of grapevines, and plenty of outdoor spaces to enjoy your drink, it's a chance to experience a different side of Cape Cod beyond the beaches and village streets.

The vineyard produces a variety of wines, including bottles in its recognizable lighthouse-shaped packaging. They're fun to bring home as a souvenir, especially if your closet can’t hold any more T-shirts.

Truro Vineyards is also home to South Hollow Spirits, so if one of you prefers gin or rum to wine, you can still find something to enjoy.

Depending on the season, you can book a tasting, explore the grounds, or enjoy food and drinks outside from the on-site food truck.

Our advice? Don’t drive all the way to North Truro just for a quick tasting. Make a day of it! Spend some time at Head of the Meadow Beach or Coast Guard Beach, where you can walk along the sand and watch the waves roll in. Or, take a walk around Highland Light and enjoy the views.

Afterward, continue north to Provincetown, explore Commercial Street, stop for dinner, and enjoy the beauty of the Outer Cape. It's a longer outing from Yarmouth Port, but with a winery visit, beach time, and a stop in Provincetown, you can easily turn it into a full day.

4 Oxbow Road, East Falmouth

Over in East Falmouth, Cape Cod Winery has a casual, welcoming setup, with outdoor seating and special events that may include live music and food vendors. Explore the winery’s selection of reds, whites, and rosés, then find a spot outside to enjoy your choice. There's also an on-site food truck serving during operating hours, with a menu that changes seasonally. Check ahead for current tasting options, since the experience and operating schedule can change with the season.

You could also spend some time exploring downtown Falmouth, browse the shops along Main Street, or stop near the waterfront before your tasting.

A couple of things to know before you go: seating is first come, first served, and the winery isn't currently accepting reservations. Tables have a two-hour limit when there's a wait, though you can stay longer if tables are available.

13 Willow Street, Yarmouth Port

Now, this one is right in our neighborhood, and it’s a great little find.

Dunn & Sons Wine isn’t a vineyard. It’s an independent wine shop with a thoughtfully selected collection of bottles from smaller producers. If you’re someone who enjoys trying wines you don’t see at every grocery store, you’ll want to stop in.

The shop also hosts complimentary Saturday wine tastings, so you can try a few before committing to a bottle. They also regularly host classes and workshops on site. Some are wine-related, some are not, but they all offer a fun way to learn something new! Check their calendar before your visit to see what’s available.

But here’s why we especially like having Dunn & Sons nearby.

You can pick up a bottle and enjoy a glass back at the inn. No restaurant reservation, no driving across the Cape, and no need to change out of whatever you’ve been wearing all afternoon.

Sometimes that’s exactly what a getaway calls for.

43 Main Street, Yarmouth Port

Italian food and a good bottle of wine. Hard to argue with that combination.

Leonessa brings Italian-inspired cooking to Yarmouth Port, with a wine list that’s especially fun to explore if you enjoy Italian reds. You’ll find everything from Chianti Classico to Nebbiolo and Barolo, along with crisp Italian whites and sparkling wines.

If you’re not sure what to order, start with the wine list and find something that catches your eye, then ask your server what they’d pair with it.

587 Main Street, Dennis Port

If you love the idea of letting the chef decide what’s for dinner, LUNE should be on your list.

Run by a husband-and-wife team, LUNE takes a different approach to dining. Instead of choosing from a traditional menu, you’ll enjoy a tasting menu that changes weekly to highlight seasonal ingredients and the best of what’s available locally. Just note that Sundays are typically à la carte only, so if you want the full tasting menu experience, make sure to visit Thursday-Saturday.

And here’s the part wine lovers will appreciate. LUNE offers an optional six-wine pairing, with each wine carefully selected to complement a course. No guessing which wine goes with what. They’ve already done the work for you.

In 2025, LUNE was named a James Beard Award semifinalist for Best New Restaurant, which is quite an achievement for this small Cape Cod restaurant.

Just make sure to make your reservations in advance!

223 Route 6A, Yarmouth Port

You can't talk about dining in Yarmouth Port without mentioning Old Yarmouth Inn. The building dates back to 1696, and the restaurant has been welcoming diners for generations. It's one of those places where you can enjoy a good meal and a little Cape Cod history at the same time.

There are two ways to enjoy it. The dining room is a good choice when you're in the mood for a leisurely dinner, while the tavern is perfect for a more casual evening. Both give you a chance to explore the restaurant's extensive wine list, whether you're ordering a glass with dinner or choosing a bottle to share.

If you're someone who likes to read through the wine list before deciding what to eat, you'll be right at home here. And if you're not, don't hesitate to ask for a recommendation.

Before you start planning your wine adventures, a few things worth knowing.

· Pick one winery for the day. Truro Vineyards and Cape Cod Winery are both great choices, but they’re too far apart to make visiting both a relaxing afternoon. Choose one and explore the surrounding area. You really can’t go wrong with either.

· Check hours and tasting options before you leave. These spots are all open year-round, but schedules, events, and food service can change throughout the year. Check the website before heading out, especially if you're visiting in the quieter months.

· Plan your ride ahead of time. If you're planning to enjoy several tastings or drinks with dinner, arrange a designated driver or other transportation before you go.

· Don’t overlook the local wine shops. A vineyard visit is fun, but it's not the only way to find a new favorite. Dunn & Sons is proof of that.

We love a good winery outing, but we also love the simple pleasure of bringing a bottle back to the inn after a day on Cape Cod.

Maybe you found a new favorite at Truro Vineyards. Maybe you stopped at Dunn & Sons and picked something more familiar. Either way, our property is the perfect place to enjoy it. You can settle into our indoor common area with a good book or a board game, retreat to your private room, or gather around the outdoor fire pit.

And if you’re still deciding which Cape Cod winery to visit or where to make dinner reservations, just ask us. Sharing our favorite local places is one of the best parts of being innkeepers.

Ready to plan your Cape Cod getaway? Explore our rooms at the Inn on Main, and we’ll help you find plenty of good things to eat, drink, and discover while you’re here.