This week, Annapolis boasts outdoor painting classes, a gentlemen-only bourbon tasting event, Navy football, and plenty more forms of entertainment. From live arts to outdoorsy fun, Annapolis has it all!

Annapolis Entertainment

The biggest event this week is the U.S. Sailboat Show–big in terms of volume and in anticipation. The sailboat shows have been hosted by Annapolis for decades and it seems that every year, the shows get better, larger, and even greener. This year’s event includes new features, more recycling, and more exciting aspects. The show begins on the 9th and ends on the 13th. Most days, the show runs from 10 a.m. to 6:30 p.m., but defer to www.usboat.com, the organizer, for complete details. Be a part of this hugely important, vastly cool event.

This Saturday, Navy plays VMI in a football game. The USNA Band will be in attendance to heighten the experience with its clanging symbols, booming drums, and resounding tunes. Learn more about this very Annapolis event at www.usna.edu. The game starts at noon in Annapolis.

Compass Rose Theatre continues their stunning, moving performance of the classic A Raisin in the Sun, winner of four Tony awards. This heartfelt play contains life lessons about family values, hardship, and more. The performance ends on October 19. To learn more and purchase tickets, visit www.compassrosetheatre.org.

Painting is often therapeutic, and painting in the gardens at the William Paca House is certainly therapeutic, lovely, and even educational. A seasoned watercolorist will conduct a painting class in the garden on Saturday, October 11, that’s open to all. Let the immaculate landscape inspire you to artsy greatness with this instructional class! Tickets per person cost $75. The class begins at 9 a.m. and ends after the lunch hour. Go to www.annapolis.org to read more.

If you prefer to fulfill an artistic void with music, consider attending the Carmina Burana, a live performance presented by Live Arts Maryland, held at Maryland Hall for the Creative Arts. This performance welcomes world-class, incredibly talented and passionate musicians, to the stage for an unforgettable night of music. Saturday night hosts this event. The show begins at 8 p.m. Tickets run from $12 to $37. Look to www.marylandhall.org to discover additional details.

Annapolis Families

The coming of fall means a few things in Annapolis: the boat shows, haunted tours, and, most importantly for families, fall festivals! This Saturday, it’s the Anne Arundel County Famers Market Pumpkin Festival at the market on Truman Parkway. Kids will enjoy fall-themed fun with this festival. The festival runs from 7 a.m. to 1 p.m. Head to http://fourriversheritage.org to learn more.

Annapolis Green

Captain Avery Museum hosts an educational and Earth-inspired lecture this week from 7 p.m. to 9 p.m. The event features a knowledgeable speaker who will discuss climate change and the rising atmospheric CO2 levels. The price is $15 per person. The ticket includes refreshments like coffee and desserts. Look to http://fourriversheritage.org for additional info.

Annapolis History

Here’s an event that’s ideal for gentleman, scholars, and good judges of whiskey (as the old adage goes): Historic Annapolis’s “Blazers, Bourbon, and Cigars.” This gentlemen-only social event includes networking with Annapolis guys, trying cigars, enjoying more than a dozen types of bourbon, eating delectable food, and more. The price for this utterly classy event is $150 for the general public. The event takes place at the William Paca House on Tuesday from 6 to 10 p.m. Head to www.annapolis.org to learn more and buy tickets.

The William Paca House also hosts a Historic Hauntings Tour this Friday night from 7:30 to 9 p.m., a night full of the retelling of Annapolis’s spooky past. This event is in celebration of Halloween. Go to www.annapolis.org to learn more.