Lifestyle Events in Annapolis

Check out happening lifestyle events all around Annapolis, MD

Hello Kitty Cafe Truck East - Annapolis Appearance

 Sat, 16 Aug at 10:00 am Annapolis Mall

The Amish Outlaws return to Rams Head On Stage

 Fri, 17 Oct at 08:00 pm Rams Head On Stage

Pilates! In The! Park!: Sunset Edition

 Sat, 23 Aug at 07:00 pm Quiet water Free

Maggiano's Annapolis Presents our Prisoner Wine Dinner

 Thu, 21 Aug at 06:30 pm Maggiano's Little Italy Annapolis USD 106

CLASSIC MOVIE NIGHT at REYNOLDS TAVERN

 Sun, 14 Sep at 08:00 pm 7 Church Cir, Annapolis, MD, United States, Maryland 21401

DJ VER1TAS at Charthouse Prime Restaurant Annapolis

 Sat, 23 Aug at 06:00 pm Charthouse Restaurant Annapolis

Hollywood Farm

 Sat, 13 Sep at 03:00 pm Annapolis Md

¿Cómo andas con el amor hacia ti misma?

 Thu, 11 Dec at 06:30 pm 2158 Renard Ct Free

Vino & Vinyasa with Lindsay Cook at Great Frogs Winery

 Thu, 21 Aug at 06:00 pm Great Frogs Winery USD 29 to 45

Fin Del Verano 2025

 Sun, 31 Aug at 04:00 pm Watermark Tours, Charters, Cruises- Annapolis City Dock USD 151

Old Fox Bibliophiles Book Club

 Wed, 20 Aug at 07:00 pm 35 Maryland Avenue, Annapolis, MD, United States, Maryland 21401

Tides & Tunes

 Tue, 19 Aug at 05:00 pm The Westin Annapolis Free

NEW Whiskey & Cigar Night @ The Lodge Annapolis!

 Fri, 22 Aug at 04:00 pm The Lodge Annapolis

Rock & Roam - A Fashion, Wine & Travel Event

 Sat, 30 Aug at 02:00 pm Local by Design at the Gallery 1805D Virginia St. Annapolis MD

Tides & Tunes

 Tue, 26 Aug at 05:00 pm The Westin Annapolis Free

Ballet in the Garden at the Hammond Harwood House

 Sun, 21 Sep at 05:00 pm Hammond-Harwood House USD 0 to 85

FOOD TRUCK NITE at the Annapolis Farmers Market - Sweet Satisfaction

 Fri, 22 Aug at 04:00 pm Food Truck Fridays Annapolis

Sacred Abundance Workshop with Rev. Sarah Phillips

 Thu, 18 Sep at 06:30 pm 4 Pointless Forest Trl, Annapolis, MD, United States, Maryland 21409

DJ VER1TAS at Charthouse Prime Restaurant Annapolis

 Fri, 26 Sep at 06:00 pm Charthouse Restaurant Annapolis

Tides & Tunes

 Tue, 02 Sep at 05:00 pm The Westin Annapolis Free

Celebrate You

 Sat, 27 Sep at 08:30 am Annapolis Town Center Free

Tides & Tunes

 Tue, 09 Sep at 05:00 pm The Westin Annapolis Free

Wellness Market

 Sat, 08 Nov at 10:00 am The Collective Free

Tides & Tunes

 Tue, 16 Sep at 05:00 pm The Westin Annapolis Free

The Pleasure Series Part 3: Energy for Better S/x

 Sun, 05 Oct at 04:00 pm Prana Studio, West Street, Annapolis, MD, USA USD 117 to 290

CLASSIC MOVIE NIGHT at REYNOLDS TAVERN

 Sun, 19 Oct at 06:00 pm 7 Church Cir, Annapolis, MD, United States, Maryland 21401

Tides & Tunes

 Tue, 23 Sep at 05:00 pm The Westin Annapolis Free

Vino & Vinyasa with Lindsay Cook at Great Frogs Winery

 Thu, 09 Oct at 06:00 pm Great Frogs Winery USD 29 to 45

7th Annual Bubbly Bridal Expo & 1000+ Gown Sale!

Sun, 23 Nov at 12:00 pm Graduate Annapolis

Tide's & Tunes

 Tue, 30 Sep at 05:00 pm The Westin Annapolis Free

Sunrise Paddle

 Sat, 16 Aug at 06:00 am 655 Americana Dr, Annapolis, MD 21403, United States

Tides & Tunes

 Tue, 07 Oct at 05:00 pm The Westin Annapolis Free

Tides & Tunes

 Tue, 14 Oct at 05:00 pm The Westin Annapolis Free

Annapolis First Sunday Arts Festival w/ The Accidental Poet

 Sun, 05 Oct at 11:00 am West St, Annapolis, MD 21401, United States

Tides & Tunes

 Tue, 21 Oct at 05:00 pm The Westin Annapolis Free

Tides & Tunes

 Tue, 28 Oct at 05:00 pm The Westin Annapolis Free

2025 Bay Bridge Run 10K

 Sun, 09 Nov at 05:30 am Annapolis, MD

Annapolis RUN for The Light House

 Sun, 14 Sep at 08:00 am Quiet Waters Park Rd, Annapolis, MD 21403, United States

Summer Camp at Andy Smith Session 6

 Mon, 18 Aug at 09:00 am 584 Broadneck Rd, Annapolis, MD 21409-5504, United States

Crack The Sky

 Thu, 30 Oct at 07:00 pm Rams Head On Stage

Annapolis Pickleball Club Bay Capital Mortgage Open September 12-14, 2025!

 Fri, 12 Sep at 12:30 pm Truxtun Park Tennis Court .

Tim O'Brien

 Sat, 16 Aug at 07:00 pm Rams Head On Stage

Sunday Peaceful Yoga in Downtown Annapolis

 Thu, 30 May at 12:00 pm 17 Francis St Free

Girls' Night at P.F. Chang's Annapolis

 Wed, 21 May at 07:00 pm 307 Sail Pl

Weekend Vibes at P.F. Chang's Annapolis

 Thu, 22 May at 11:00 am 307 Sail Pl Free