Day Trips from Gloucester
← All Gloucester day tripsDay Trips from Gloucester: Wineries & Vineyards
Discover the best wineries and vineyards within driving distance of Gloucester, MA. From intimate tasting rooms to sprawling estate vineyards, these destinations make for a perfect day trip or weekend wine getaway. Real drive times, ratings, and booking links included.
12 wineries near Gloucester
Willow Spring Vineyards
Haverhill, MA 01832
Just 52 min from Gloucester, rated 4.9 stars, known for excellent food, drink, and local flavor.
Best time to visit: Year-round, but harvest season (Sep-Oct) is peak for wineries and farm-to-table.
Averill House Vineyard
Brookline, NH 03033
Just 1 hr 20 min from Gloucester, rated 4.9 stars by 342 visitors, known for excellent food, drink, and local flavor.
Best time to visit: Year-round, but harvest season (Sep-Oct) is peak for wineries and farm-to-table.
Cellardoor Winery Portland
Portland, ME 04101
Just 1 hr 42 min from Gloucester, rated 4.8 stars by 116 visitors, known for excellent food, drink, and local flavor.
Best time to visit: Year-round, but harvest season (Sep-Oct) is peak for wineries and farm-to-table.
Nasketucket Bay Vineyard & Distillery
Fairhaven, MA 02719
Just 1 hr 44 min from Gloucester, rated 4.8 stars by 159 visitors, a popular destination with plenty to see and do.
Best time to visit: Spring and fall offer mild weather and smaller crowds at most attractions.
Sunset Meadow Vineyards
Goshen, CT 06756
Just 2 hrs 57 min from Gloucester, rated 4.8 stars by 418 visitors, known for excellent food, drink, and local flavor.
Best time to visit: Year-round, but harvest season (Sep-Oct) is peak for wineries and farm-to-table.
Vista of Maine Vineyard & Cidery Tasting Room, Wedding barn .
Greene, ME 04236
Just 2 hrs 21 min from Gloucester, rated 4.8 stars, known for excellent food, drink, and local flavor.
Best time to visit: Year-round, but harvest season (Sep-Oct) is peak for wineries and farm-to-table.
Mulberry Vineyards
Chepachet, RI 02814
Just 1 hr 46 min from Gloucester, rated 4.8 stars, known for excellent food, drink, and local flavor.
Best time to visit: Year-round, but harvest season (Sep-Oct) is peak for wineries and farm-to-table.
Marble Ridge Winery
North Andover, MA 01845
Just 42 min from Gloucester, rated 4.8 stars, known for excellent food, drink, and local flavor.
Best time to visit: Year-round, but harvest season (Sep-Oct) is peak for wineries and farm-to-table.
Black Bear Vineyard
Salisbury, NH 03268
Just 1 hr 46 min from Gloucester, rated 4.8 stars by 106 visitors, packed with outdoor activities and adventure.
Best time to visit: Spring through fall for most outdoor activities. Winter for snow sports where available.
Seven Birches Winery
Lincoln, NH 03251
Just 2 hrs 14 min from Gloucester, rated 4.7 stars by 211 visitors, known for excellent food, drink, and local flavor.
Best time to visit: Year-round, but harvest season (Sep-Oct) is peak for wineries and farm-to-table.
Zorvino Vineyards
Sandown, NH 03873
Just 1 hr 9 min from Gloucester, rated 4.7 stars by 408 visitors, known for excellent food, drink, and local flavor.
Best time to visit: Year-round, but harvest season (Sep-Oct) is peak for wineries and farm-to-table.
Mill River Winery
Rowley, MA 01969
Just 30 min from Gloucester, rated 4.6 stars by 129 visitors, known for excellent food, drink, and local flavor.
Best time to visit: Year-round, but harvest season (Sep-Oct) is peak for wineries and farm-to-table.
Frequently Asked Questions About Wineries Day Trips from Gloucester
What are the best wineries near Gloucester, MA?
The best wineries near Gloucester include award-winning vineyards, tasting rooms, and estate wineries all within a few hours' drive. Check the destination cards above for ratings, drive times, and direct booking links.
Are there wine tours near Gloucester?
Yes. Many wineries near Gloucester offer guided tastings and tours. Use the "Book Activities" button on any card to find wine tour packages through Viator and GetYourGuide, which often include transportation and multi-winery stops.
How far are the closest wineries from Gloucester?
The closest wineries to Gloucester are typically 45 minutes to 2 hours away, making them ideal for a day trip. Some regions farther out (2-3 hours) are worth an overnight stay for a full wine weekend.
What is the best time to visit wineries near Gloucester?
Fall harvest season (September-October) is peak time for wineries, with grape picking and crush events. Spring and summer offer beautiful vineyard scenery. Most tasting rooms are open year-round, and winter visits mean smaller crowds and more personal attention.
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