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Wineries Offering Wine by the Glass in Maryland

5 of the 144 wineries we track in Maryland have wine by the glass available. Full listings for every city are on the Maryland page.

5wineries
5cities
144wineries statewide

This directory features wineries and tasting rooms that offer individual glass pours alongside standard tasting flights. Visitors can order full 5-ounce glasses ranging from current releases to reserve vintages without committing to a full bottle purchase. Many featured locations serve pours in varietal-specific Riedel or crystal glassware for optimal tasting.

Annapolis 1

  1. Cooper's Hawk Winery and Restaurant

    1906 Towne Centre Blvd, Annapolis, MD 21401-3676

    Mon-Thu 11am-9pm, Fri-Sun 10am-10pm

    TastingsFood servedPrivate events
    Call Website All Annapolis

Leonardtown 1

  1. Port of Leonardtown Winery

    23190 Newtowne Neck Rd, Leonardtown, MD 20650

    Daily 12-6pm

    TastingsPrivate events
    Call Website All Leonardtown

Mechanicsville 1

  1. Xella Winery and Vineyard

    26781 Laurel Grove Rd, Mechanicsville, MD 20659-5453

    Sat-Sun 12-5pm

    TastingsPrivate events
    Call Website All Mechanicsville

New Market 1

  1. New Market Plains Vineyards

    11111 W Baldwin, New Market, MD 21774

    Fri 12-5, Sat 12-6, Sun 12-5

    TastingsFood servedOutdoor seatingPrivate events
    Call Website

Rockville 1

  1. Cooper's Hawk Winery & Restaurant

    1403 Research Blvd, Rockville, MD 20850-3876

    Mon-Thu 11-9, Fri 11-10, Sat 10-10, Sun 10-9

    TastingsFood servedPrivate events
    Call Website
Patio seating limits apply: Some estate wineries restrict by-the-glass service to designated patio or lawn areas and require bottle purchases for indoor seated tasting areas.

Also in Maryland

Good to know

How much does a glass of wine cost at a winery tasting room?

A standard 5-ounce glass of current vintage wine at US tasting rooms costs between $12 and $22. Reserve bottles, single-vineyard designates, or estate sparkling wines poured in crystal glassware typically range from $25 to $45 per glass.

Do I need a reservation to order wine by the glass?

While weekday walk-ins for glass service are common, roughly 60% of estate wineries require advance reservations on Fridays through Sundays. Unreserved glass-pour seating is often limited to outdoor picnic tables or lawn areas on a first-come, first-served basis.

Can I bring my own crystal glassware or wine markers to the winery?

Wineries provide their own varietal glassware (such as Riedel or Schott Zwiesel) and generally prohibit outside glass containers for safety and liability reasons. Removable silicone wine glass markers or glass charms are permitted at informal lawn seating areas, but staff prefer guests use provided glassware without modification.

Is Napa or Sonoma better?

Napa Valley is generally known for luxury estate experiences and Cabernet Sauvignon, while Sonoma County offers a more relaxed, rustic atmosphere with diverse microclimates. Choosing between them depends on whether you prefer high-end luxury or informal country vineyards. You can explore 5 top wine destinations across Maryland on WineryAtlas.

How to find cheap weekend getaways?

Look for tasting rooms and boutique vineyard stays in emerging wine regions rather than major tourist centers, and book mid-week or off-peak seasons. Visiting local tasting rooms offers affordable entertainment and regional culture. Discover budget-friendly wine getaways across 5 locations in Maryland.